Condensed cyclic compound and organic light-emitting device including the same

Abstract

A condensed cyclic compound represented by Formula 1: wherein in Formula 1, Ar 1 and R 1 to R 8 are the same as described in the specification.

What is claimed is: 
     
         1 . A condensed cyclic compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein Ar 1  in Formula 1 is selected from groups represented by Formulae 2A to 2C, 
         R 13  and R 15  in Formulae 2A to 2C are optionally connected to each other through *—O—*′, *—S—*′, *—C(R 31 )(R 32 )—*′, or *—Si(R 31 )(R 32 )—*′ to form a 5-membered ring, 
         R 11  and R 14  in Formulae 2A to 2C are optionally connected to each other through *—O—*′, *—S—*′, *—C(R 33 )(R 34 )—*′, or *—Si(R 33 )(R 34 )—*′ to form a 5-membered ring, 
         R 15  and R 22  in Formulae 2A and 2B are optionally connected to each other through *—O—*′, *—S—*′, *—C(R 35 )(R 36 )—*′, or *—Si(R 35 )(R 36 )—*′ to form a 5-membered ring, 
         R 16  and R 21  in Formulae 2A and 2B are optionally connected to each other through *—O—*′, *—S—*′, *—C(R 37 )(R 38 )—*′, or *—Si(R 37 )(R 38 )—*′ to form a 5-membered ring, 
         R 24  and R 27  in Formula 2B are optionally connected to each other through *—O—*′, *—S- 13  *′, *—C(R 39 )(R 40 )—*′, or *—Si(R 39 )(R 40 )—*′ to form a 5-membered ring, 
         R 21  and R 26  in Formula 2B are optionally connected to each other through *—O—*′, *—S—*′, *—C(R 41 )(R 42 )—*′, or *—Si(R 41 )(R 42 )—*′ to form a 5-membered ring, 
         R 1  to R 8 , R 11  to R 17 , R 21  to R 30 , and R 31  to R 42  in Formulae 1 and 2A to 2C are each independently selected from: 
         hydrogen, deuterium, a cyano group, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group; 
         a C 1 -C 20  alkyl group and a C 1 -C 20  alkoxy group, each substituted with at least one selected from deuterium and a cyano group; and 
         a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzosilolyl group, each substituted with at least one of deuterium, a cyano group, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group; 
         Ar 2  in Formula 2C is selected from 
         a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group; and 
         a dibenzofuranyl group, a dibenzothiophenyl group and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a cyano group, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, and 
         * indicates a binding site to an adjacent atom. 
       
     
     
         2 . The condensed cyclic compound of  claim 1 , wherein
 Ar 1  is selected from groups represented by Formulae 2A-1 to 2A-4:   
       
         
           
           
               
               
           
         
         wherein, in Formulae 2A-1 to 2A-4, 
         X 1  is O, S, C(R 31 )(R 32 ), or Si(R 31 )(R 32 ), 
         X 2  is O, S, C(R 33 )(R 34 ), or Si(R 33 )(R 34 ), 
         X 3  is O, S, C(R 35 )(R 36 ), or Si(R 35 )(R 36 ), 
         X 4  is O, S, C(R 37 )(R 38 ), or Si(R 37 )(R 38 ), 
         R 11  to R 17 , R 21  to R 25 , and R 31  to R 38  are the same as in  claim 1 , and 
         * indicates a binding site to an adjacent atom. 
       
     
     
         3 . The condensed cyclic compound of  claim 1 , wherein
 Ar 1  is selected from groups represented by Formulae 2B-1 to 2B-6:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formulae 2B-1 to 2B-6, 
         X 1  is O, S, C(R 31 )(R 32 ), or Si(R 31 )(R 32 ), 
         X 2  is O, S, C(R 33 )(R 34 ), or Si(R 33 )(R 34 ), 
         X 3  is O, S, C(R 35 )(R 36 ), or Si(R 35 )(R 36 ), 
         X 4  is O, S, C(R 37 )(R 38 ), or Si(R 37 )(R 38 ), 
         X 5  is O, S, C(R 39 )(R 40 ), or Si(R 39 )(R 40 ), 
         X 6  is O, S, C(R 41 )(R 42 ), or Si(R 41 )(R 42 ), 
         R 11  to R 17 , R 21  to R 30 , and R 31  to R 42  are the same as in  claim 1 , and 
         * indicates a binding site to an adjacent atom. 
       
     
     
         4 . The condensed cyclic compound of  claim 1 , wherein
 R 1  to R 8 , R 11  to R 17 , R 21  to R 30 , and R 31  to R 42  are each independently selected from   hydrogen, deuterium, a cyano group, a C 1 -C 20  alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group;   a C 1 -C 20  alkyl group substituted with at least one of deuterium and a cyano group; and   a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a cyano group, a C 1 -C 20  alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group.   
     
     
         5 . The condensed cyclic compound of  claim 1 , wherein R 1  to R 8 , R 11  to R 17 , R 21  to R 30 , and R 31  to R 42  are each independently selected from hydrogen, deuterium, a cyano group, and groups represented by Formulae 4-1 to 4-29: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein * in Formulae 4-1 to 4-29 indicates a binding site to an adjacent atom. 
       
     
     
         6 . The condensed cyclic compound of  claim 1 , wherein at least one of R 1  and R 2  in Formula 1 is a cyano group. 
     
     
         7 . The condensed cyclic compound of  claim 1 , wherein
 each of R 11  to R 17  and R 21  to R 25  in Formula 2A is simultaneously hydrogen, or   at least one of R 23 , R 25 , and R 15  to R 17  in Formula 2A is each independently selected from a cyano group and groups represented by Formulae 4-1 to 4-29, or   each of R 11  to R 17 , R 21  to R 24 , and R 26  to R 30  in Formula 2B is simultaneously hydrogen, or   at least one of R 15 , R 17 , R 21 , R 23 , R 28 , and R 30  in Formula 2B is each independently selected from a cyano group and groups represented by Formulae 4-1 to 4-29, or   R 17  in Formula 2C is a cyano group, a phenyl group, a biphenyl group or a terphenyl group,   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formulae 4-1 to 4-29, * indicates a binding site to an adjacent atom. 
       
     
     
         8 . The condensed cyclic compound of  claim 2 , wherein
 i) at least one of R 17  and R 25  in Formula 2A-1,   ii) at least one of R 17  and R 25  in Formula 2A-2,   iii) R 17  in Formula 2A-3, and   iv) R 17  in Formula 2A-4 are each independently selected from a cyano group and groups represented by Formulae 4-1 to 4-29:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formula 4-1 to 4-29, * indicates a binding site to an adjacent atom. 
       
     
     
         9 . The condensed cyclic compound of  claim 3 , wherein
 i) R 17  in Formula 2B-1,   ii) R 17  in Formula 2B-2,   iii) one of R 17  and R 28  in Formula 2B-3,   iv) one of R 17  and R 28  in Formula 2B-4,   v) one of R 23 , R 28 , and R 30  in Formula 2B-5, and   vi) one of R 23 , R 28 , and R 30  in Formula 2B-6 are each independently selected from a cyano group and groups represented by Formulae 4-1 to 4-29:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formulae 4-1 to 4-29, * indicates a binding site to an adjacent atom. 
       
     
     
         10 . The condensed cyclic compound of  claim 1 , wherein the number of cyano groups in each of Formulae 2A to 2C is 1, 2, 3, or 4. 
     
     
         11 . The condensed cyclic compound of  claim 1 , wherein the condensed cyclic compound has a difference between a triplet (T 1 ) energy level and a singlet (S 1 ) energy level in a range from about 0.1 electron Volts to about 0.6 electron Volts. 
     
     
         12 . The condensed cyclic compound of  claim 1 , wherein the condensed cyclic compound has a triplet (T 1 ) energy level in a range from about 2.9 electron Volts to about 3.1 electron Volts. 
     
     
         13 . The condensed cyclic compound of  claim 1 , wherein the condensed cyclic compound is one selected from Compounds 1 to 116: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         14 . An organic light-emitting device comprising:
 a first electrode;   a second electrode; and   an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 of  claim 1 .   
     
     
         15 . The organic light-emitting device of  claim 14 , wherein
 the first electrode is an anode,   the second electrode is a cathode, and   the organic layer comprises
 a hole transport region disposed between the first electrode and the emission layer, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and 
 an electron transport region disposed between the emission layer and the second electrode, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. 
   
     
     
         16 . The organic light-emitting device of  claim 14 , wherein the emission layer comprises the at least one condensed cyclic compound represented by Formula 1. 
     
     
         17 . The organic light-emitting device of  claim 16 , wherein the emission layer further comprises a phosphorescent dopant comprising an organometallic compound represented by Formula 81: 
       
         
           
           
               
               
           
         
         wherein, in Formulae 81 and 81A, 
         M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh, 
         L 81  is a ligand represented by Formula 81A, 
         n81 is an integer selected from 1 to 3, provided that when n81 is 2 or greater, two or more groups L 81  are identical to or different from each other, 
         L 82  is an organic ligand, 
         n82 is an integer selected from 0 to 4, provided that when n82 is 2 or greater, two or more groups L 82  are identical to or different from each other, 
         Y 81  to Y 84  are each independently C or N, 
         Y 81  and Y 82  are linked to each other via a single bond or a double bond, and Y 83  and Y 84  are linked to each other via a single bond or a double bond, 
         CY 81  and CY 82  are each independently selected from a C 5 -C 30  carbocyclic group and a C 3 -C 30  hetero carbocyclic group, 
         CY 81  and CY 82  are optionally further linked to each other via an organic linking group, 
         R 81  to R 85  are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF 5 , a substituted or unsubstituted C 1 -C 60  alkyl group, a substituted or unsubstituted C 2 -C 60  alkenyl group, a substituted or unsubstituted C 2 -C 60  alkynyl group, a substituted or unsubstituted C 1 -C 60  alkoxy group, a substituted or unsubstituted C 3 -C 10  cycloalkyl group, a substituted or unsubstituted C 1 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 1 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 6 -C 60  aryloxy group, a substituted or unsubstituted C 6 -C 60  arylthio group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 81 )(Q 82 )(Q 83 ), —N(Q 84 )(Q 85 ), —B(Q 86 )(Q 87 ), and —P(═O)(Q 88 )(Q 89 ), 
         a81 to a83 are each independently an integer selected from 0 to 5, provided that 
         when a81 is 2 or greater, two or more groups R 81  are identical to or different from each other, 
         when a82 is 2 or greater, two or more groups R 82  are identical to or different from each other, 
         when a81 is 2 or greater, adjacent groups R 81  are optionally linked to each other to form a saturated or unsaturated ring, 
         when a82 is 2 or greater, adjacent groups R 82  are optionally linked to each other to form a saturated or unsaturated ring, 
         wherein in Formula 81A, * and *′ each indicate a binding site to M in Formula 81, 
         wherein at least one of substituents of the substituted C 1 -C 60  alkyl group, substituted C 2 -C 60  alkenyl group, substituted C 2 -C 60  alkynyl group, substituted C i -C 60  alkoxy group, substituted C 3 -C 10  cycloalkyl group, substituted C 1 -C 10  heterocycloalkyl group, substituted C 3 -C 10  cycloalkenyl group, substituted C 1 -C 10  heterocycloalkenyl group, substituted C 6 -C 60  aryl group, substituted C 6 -C 60  aryloxy group, substituted C 6 -C 80  arylthio group, substituted C 1 -C 60  heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from : 
         deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -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 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 91 )(Q 92 )(Q 93 ), 
         wherein Q 81  to Q 89  and Q 91  to Q 93  are each independently selected from hydrogen, deuterium, a C 1 -C 60  alkyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C i -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. 
       
     
     
         18 . The organic light-emitting device of  claim 17 , wherein Y 81  is N, Y 82  and Y 83  are each C, and Y 84  is N or C,
 wherein CY 81  and CY 82  are each independently selected from a cyclopentadiene, a benzene, a heptalene, an indene, a naphthalene, an azulene, an indacene, an acenaphthylene, a fluorene, a spiro-bifluorene, a benzofluorene, a dibenzofluorene, a phenalene, a phenanthrene, an anthracene, a fluoranthene, a triphenylene, a pyrene, a chrysene, a naphthacene, a picene, a perylene, a pentacene, a hexacene, a pentaphene, a rubicene, a coronene, an ovalene, a pyrrole, an isoindole, an indole, an indazole, a pyrazole, an imidazole, a triazole, an oxazole, an isoxazole, an oxadiazole, a thiazole, an isothiazole, a thiadiazole, a purine, a furan, a thiophene, a pyridine, a pyrimidine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzoimidazole, a benzofuran, a benzothiophene, an isobenzothiazole, a benzoxazole, an isobenzoxazole, a benzocarbazole, a dibenzocarbazole, an imidazopyridine, an imidazopyrimidine, a dibenzofuran, a dibenzothiophene, a dibenzothiophene sulfone, a carbazole, a dibenzosilole, and a 2,3-dihydro-1 H-imidazole.   
     
     
         19 . The organic light-emitting device of  claim 17 , wherein in Formula 81A, at least one selected from a81 number of groups R 81  and a82 number of groups R 82  is a cyano group or deuterium. 
     
     
         20 . The organic light-emitting device of  claim 16 , wherein the emission layer emits blue light.