Organometallic compound and organic light-emitting device including the same

Abstract

An organometallic compound represented by Formula 1 and an organic light-emitting device including the same: Y 2 , ring A 2 , R 1 to R 8 , R 13 to R 20 , and d2 in Formula 1 may be each independently the same as described in the specification.

What is claimed is: 
     
         1 . An organometallic compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         Y 2  is C, 
         ring A 2  is a C 5 -C 30  carbocyclic group or a C 1 -C 30  heterocyclic group, 
         R 1  to R 8 , R 13  to R 17 , and R 20  are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 2 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 10  aryl group, a substituted or unsubstituted C 6 -C 10  aryloxy group, a substituted or unsubstituted C 6 -C 10  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, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 >, or —P(Q 8 )(Q 9 ), 
         d2 is an integer from 0 to 10, and when d2 is 2 or more, two or more R 20 (s) are identical to or different from each other, 
         i) at least one of R 1  to R 8  is —CH 2 F, —CHF 2  or —CF 3 , and ii) R 20  comprises neither a fluoro group (—F) nor a cyano group, 
         R 18  and R 19  are each independently a substituted or unsubstituted C 2 -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 2 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 10  aryl group, a substituted or unsubstituted C 6 -C 10  aryloxy group, a substituted or unsubstituted C 6 -C 10  arylthio group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, 
         two or more of R 1  to R 8  are optionally linked to form a C 5 -C 30  carbocyclic group which is unsubstituted or substituted with at least one R 1a  or a C 1 -C 30  heterocyclic group which is unsubstituted or substituted with at least one R 1a , 
         two or more of R 20 (s) in the number of d2 are optionally linked to form a C 5 -C 30  carbocyclic group which is unsubstituted or substituted with at least one R 1a  or a C 1 -C 30  heterocyclic group which is unsubstituted or substituted with at least one R 1a , 
         two or more of R 13  to R 19  are optionally linked to form a C 5 -C 30  carbocyclic group which is unsubstituted or substituted with at least one R 1a  or a C 1 -C 30  heterocyclic group which is unsubstituted or substituted with at least one R 1a , 
         R 1a  is the same as explained in connection with R 2 , 
         a substituent of the substituted C 1 -C 60  alkyl group, the substituted C 2 -C 60  alkenyl group, the substituted C 2 -C 60  alkynyl group, the substituted C 1 -C 60  alkoxy group, the substituted C 3 -C 10  cycloalkyl group, the substituted C 2 -C 10  heterocycloalkyl group, the substituted C 3 -C 10  cycloalkenyl group, the substituted C 2 -C 10  heterocycloalkenyl group, the substituted C 6 -C 10  aryl group, the substituted C 6 -C 10  aryloxy group, the substituted C 6 -C 60  arylthio group, the substituted C 1 -C 60  heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is: 
         deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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, or a C 1 -C 60  alkoxy group; 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, or a C 1 -C 60  alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 10  aryl group, a C 6 -C 10  aryloxy group, a C 6 -C 10  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof; 
         a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 10  aryl group, a C 6 -C 10  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 2 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 2 -C 10  heterocycloalkenyl group, a C 6 -C 10  aryl group, a C 6 -C 10  aryloxy group, a C 6 -C 10  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or any combination thereof; 
         —N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or 
         any combination thereof, 
         wherein Q 1  to Q 9 , Q 11  to Q 19 , Q 21  to Q 29 , and Q 31  to Q 39  are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro 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, unsubstituted or substituted with deuterium, a C 1 -C 60  alkyl group, a C 6 -C 60  aryl group, or any combination thereof; 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 2 -C 10  heterocycloalkyl group; a C 3 -C 10  cycloalkenyl group; a C 2 -C 10  heterocycloalkenyl group; a C 6 -C 10  aryl group, unsubstituted or substituted with deuterium, a C 1 -C 60  alkyl group, a C 6 -C 10  aryl group, or any combination thereof; a C 6 -C 10  aryloxy group; a C 6 -C 10  arylthio group; a C 1 -C 60  heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group. 
       
     
     
         2 . The organometallic compound of  claim 1 , wherein
 ring A 2  is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.   
     
     
         3 . The organometallic compound of  claim 1 , wherein
 R 1  to R 8 , R 13  to R 17 , and R 20  are each independently hydrogen, deuterium, —F, a substituted or unsubstituted C 1 -C 20  alkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkyl group, a substituted or unsubstituted C 2 -C 10  heterocycloalkyl group, —Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ).   
     
     
         4 . The organometallic compound of  claim 1 , wherein
 R 1  to R 8  and R 13  to R 17  are each independently:   hydrogen, deuterium, or —F;   a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, or a C 2 -C 10  heterocycloalkyl group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, or any combination thereof; or   —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ), and   R 20  is   hydrogen or deuterium;   a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, or a C 2 -C 10  heterocycloalkyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, a C 2 -C 60  heterocycloalkyl group, or any combination thereof; or   —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).   
     
     
         5 . The organometallic compound of  claim 1 , wherein
 R 18  and R 19  are each independently an unsubstituted or substituted C 2 -C 60  alkyl group, an unsubstituted or substituted C 3 -C 10  cycloalkyl group, or an unsubstituted or substituted C 2 -C 10  heterocycloalkyl group.   
     
     
         6 . The organometallic compound of  claim 1 , wherein
 R 18  and R 19  are each independently a C 2 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, or a C 2 -C 60  heterocycloalkyl group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, or any combination thereof.   
     
     
         7 . The organometallic compound of  claim 1 , wherein
 at least one of R 4  to R 8  is —CH 2 F, —CHF 2  or —CF 3 .   
     
     
         8 . The organometallic compound of  claim 1 , wherein
 one or two of R 1  to R 8  each independently is —CH 2 F, —CHF 2  or —CF 3 , and   at least one of R 1  to R 8  i) does not comprise a fluoro group (—F), and ii) is not hydrogen.   
     
     
         9 . The organometallic compound of  claim 1 , wherein
 a group represented by   
       
         
           
           
               
               
           
         
          in Formula 1 is a group represented by one of Formulae CY1 to CY88: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formulae CY1 to CY88, 
         T 4  to T 8  are each independently —CH 2 F, —CHF 2  or —CF 3 , 
         each of R 2 , R 4  to R 8 , and R 1a  are the same as described in  claim 1 , and R 2  and R 4  to R 8  are not hydrogen, 
         * indicates a binding site to Ir in Formula 1, and 
         *″ indicates a binding site to a neighboring atom in Formula 1. 
       
     
     
         10 . The organometallic compound of  claim 10 , wherein
 R 2  and R 4  to R 8  in Formulae CY1 to CY88 are each independently:   deuterium; or   a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, or a C 1 -C 10  heterocycloalkyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, a C 2 -C 60  heterocycloalkyl group, or any combination thereof.   
     
     
         11 . The organometallic compound of  claim 1 , wherein
 a group represented by   
       
         
           
           
               
               
           
         
          in Formula 1 is a group represented by one of Formulae A(1) to A(7): 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, in Formulae A(1) to A(7), 
         Y 2  is C, 
         X 2  is O, S, N(R 25 ), C(R 25 )(R 26 ), or Si(R 25 )(R 26 ), 
         each of R 9  to R 12  and R 21  to R 26  are the same as described in connection with R 20  in  claim 1 , 
         *′ indicates a binding site to Ir in Formula 1, and 
         *″ indicates a binding site to a neighboring atom in Formula 1. 
       
     
     
         12 . The organometallic compound of  claim 11 , wherein
 R 9  and R 11  in Formula A(1) are each independently a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, or a C 2 -C 10  heterocycloalkyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20  alkyl group, a C 3 -C 10  cycloalkyl group, a C 2 -C 10  heterocycloalkyl group, or any combination thereof.   
     
     
         13 . The organometallic compound of  claim 1 , wherein
 none of R 14  and R 16  is hydrogen.   
     
     
         14 . The organometallic compound of  claim 1 , wherein
 a number of carbons in a group represented by *—C(R 13 )(R 14 )(R 19 ) in Formula 1 is 5 or more, and   a number of carbons in a group represented by *—C(R 16 )(R 17 )(R 18 ) in Formula 1 is 5 or more.   
     
     
         15 . The organometallic compound of  claim 1 , wherein
 the organometallic compound is at least one of Compounds 6 to 8, 12, 17, 27, 28 and 38 below:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         16 . 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 and comprising an emission layer,   wherein the organic layer comprises at least one organometallic compound of  claim 1 .   
     
     
         17 . The organic light-emitting device of  claim 16 , wherein
 the first electrode is an anode,   the second electrode is a cathode,   the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,   the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and   the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.   
     
     
         18 . The organic light-emitting device of  claim 16 , wherein
 the organometallic compound is included in the emission layer.   
     
     
         19 . The organic light-emitting device of  claim 18 , wherein
 the emission layer emits red light.