Ink composition for organic light-emitting device, organic light-emitting device including film formed by using the ink composition, and method of manufacturing the organic light-emitting device

Abstract

An ink composition for an organic light-emitting device, the ink composition including a luminescent host material and a solvent, wherein the luminescent host material includes at least one compound represented by Formula (1), and wherein the solvent includes at least one selected from an aromatic ether, an aromatic ester, and an aromatic ketone: wherein, in Formula (1), groups and variables are the same as described in the specification.

What is claimed is: 
     
         1 . An ink composition for an organic light-emitting device, the ink composition comprising a luminescent host material and a solvent,
 wherein the luminescent host material comprises at least one compound represented by Formula (1), and   wherein the solvent comprises at least one selected from an aromatic ether, an aromatic ester, and an aromatic ketone:   
       
         
           
           
               
               
           
         
         wherein, in Formula (1), 
         L 1  to L 3  are each independently selected from a single bond, *—O—*′, *—S—*′, *—N(R 5 )—*′, a substituted or unsubstituted C 2 -C 60  alkylene group, a substituted or unsubstituted C 3 -C 10  cycloalkylene group, a substituted or unsubstituted C 1 -C 10  heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10  cycloalkenylene group, a substituted or unsubstituted C 1 -C 10  heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60  arylene group, a substituted or unsubstituted C 1 -C 60  heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, 
         a1 to a3 are each independently an integer from 1 to 10, 
         A 1  to A 3  are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , —NCS, 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 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 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), and —C(═O)(Q 1 ), 
         any neighboring groups in A 1  to A 3  are optionally linked to form a substituted or unsubstituted C 5 -C 30  carbocyclic group or a substituted or unsubstituted C 2 -C 30  heterocyclic group, 
         provided that *-(L 2 ) a2 -(A 2 ) and *-(L 3 ) a3 -(A 3 ) in Formula (1) are not hydrogen at the same time, 
         at least one substituent of the substituted C 2 -C 60  alkylene group, the substituted C 3 -C 10  cycloalkylene group, the substituted C 1 -C 10  heterocycloalkylene group, the substituted C 3 -C 10  cycloalkenylene group, the substituted C 1 -C 10  heterocycloalkenylene group, the substituted C 6 -C 60  arylene group, the substituted C 1 -C 60  heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, 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 1 -C 10  heterocycloalkyl group, the substituted C 3 -C 10  cycloalkenyl group, the substituted C 1 -C 10  heterocycloalkenyl group, the substituted C 6 -C 60  aryl group, the substituted C 6 -C 60  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, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 5 -C 30  carbocyclic group, and the substituted C 2 -C 30  heterocyclic group is selected from: 
         deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , —NCS, 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, and 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, and a C 1 -C 60  alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , —NCS, 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 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, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), and —C(═O)(Q 11 ); 
         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, and a monovalent non-aromatic condensed heteropolycyclic 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, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —C 1 , —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 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, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), and —C(═O)(Q 21 ); and 
         —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), and —C(═O)(Q 31 ), and 
         Q 1  to Q 3 , Q 11  to Q 13 , Q 21  to Q 23 , and Q 31  to Q 33  are each independently selected from hydrogen, deuterium, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a biphenyl group, a phenylpyridinyl group, a phenylpyrimidinyl group, a phenyltriazinyl group, a diphenylpyridinyl group, a diphenylpyrimidinyl group, a diphenyltriazinyl group, a pyridinylphenyl group, a dipyridinylphenyl group, a pyrimidinylphenyl group, a dipyrimidinylphenyl group, a triazinylphenyl group, a ditriazinylphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzofuranyl group, a phenyldibenzofuranyl group, a diphenyldibenzofuranyl group, a dibenzothiophenyl group, a phenyldibenzothiophenyl group, and a diphenyldibenzothiophenyl group. 
       
     
     
         2 . The ink composition of  claim 1 , wherein
 at least one of A 1  to A 3  in the at least one compound represented by Formula (1) and comprised in the luminescent host material is a group represented by Formula (2-A):   
       
         
           
           
               
               
           
         
         wherein, in Formula (2-A), 
         X 1  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 2  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 3  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 4  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 5  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; and X 6  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 , 
         at least one of X 1  to X 6  is N, 
         L 11  and L 13  are the same as described in connection with L 1  in  claim 1 , 
         a11 and a13 are the same as described in connection with a1 in  claim 1 , 
         R 11  is the same as described in connection with A 1  in  claim 1 , 
         two or more neighboring groups selected from a plurality of groups R 11  are optionally linked to form a substituted or unsubstituted C 5 -C 30  carbocyclic group or a substituted or unsubstituted C 2 -C 30  heterocyclic group, 
         b4 is an integer from 0 to 4, and 
         * indicates a binding site to a neighboring atom. 
       
     
     
         3 . The ink composition of  claim 1 , wherein
 the luminescent host material comprises at least one compound represented by Formula (2):   
       
         
           
           
               
               
           
         
         wherein, in Formula (2), L 1  to L 3 , a1 to a3, and A 1  to A 3  are each independently the same as described in  claim 1 , and at least one of A 1  to A 3  is a group represented by Formula (2-A): 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (2-A), 
         X 1  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 2  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 3  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 4  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 5  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 ; X 6  is N, carbon linked to *-(L 11 ) a11 -(R 11 ), or carbon linked to L 13 , 
         at least one of X 1  to X 6  is N, 
         L 11  and L 13  are the same as described in connection with L 1  in  claim 1 , 
         a11 and a13 are the same as described in connection with a1 in  claim 1 , 
         R 11  is the same as described in connection with A 1  in  claim 1 , 
         two or more neighboring groups selected from a plurality of groups R 11  are optionally linked to form a substituted or unsubstituted C 5 -C 30  carbocyclic group or a substituted or unsubstituted C 2 -C 30  heterocyclic group, 
         b4 is an integer from 0 to 4, and 
         * indicates a binding site to a neighboring atom. 
       
     
     
         4 . The ink composition of  claim 1 , wherein
 the luminescent host material comprises at least one compound having a biscarbazole backbone.   
     
     
         5 . The ink composition of  claim 1 , wherein
 the luminescent host material comprises at least one compound represented by Formula (3):   
       
         
           
           
               
               
           
         
         wherein, in Formula (3), L 1 , L 2 , a2, a3, A 1 , and A 2  are each independently the same as described in  claim 1 , and L 63 , a63, and A 3  are the same as described in connection with L 3 , a3, and A 3  in  claim 1 . 
       
     
     
         6 . The ink composition of  claim 5 , wherein
 L 1 , L 2 , and L 63  are each independently selected from:   a single bond; and   a phenylene group, a fluorenylene group, a spiro-bifluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, each substituted or unsubstituted with at least one selected from deuterium, —CD 3 , —CD 2 H, —CDH 2 , a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a biphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzofuranyl group, a phenyldibenzofuranyl group, a diphenyldibenzofuranyl group, a dibenzothiophenyl group, a phenyldibenzothiophenyl group, and a diphenyldibenzothiophenyl group,   a1, a2, and a63 are each independently 1, 2, or 3,   A 1 , A 2 , and A 63  are each independently selected from:   hydrogen, deuterium, —CD 3 , —CD 2 H, —CDH 2 , a C 1 -C 20  alkyl group, and a C 1 -C 20  alkoxy group; and   a phenyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted or unsubstituted with at least one selected from deuterium, —CD 3 , —CD 2 H, —CDH 2 , a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a biphenyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzofuranyl group, a phenyldibenzofuranyl group, a diphenyldibenzofuranyl group, a dibenzothiophenyl group, a phenyldibenzothiophenyl group, and a diphenyldibenzothiophenyl group.   
     
     
         7 . The ink composition of  claim 3 , wherein
 the luminescent host material further comprises at least one compound having a biscarbazole backbone.   
     
     
         8 . The ink composition of  claim 3 , wherein
 the luminescent host material further comprises at least one compound represented by Formula (3):   
       
         
           
           
               
               
           
         
         wherein, in Formula (3), L 1 , L 2 , a2, a3, A 1 , and A 2  are each independently the same as described in  claim 1 , and L 63 , a63, and A 3  are the same as described in connection with L 3 , a3, and A 3  in  claim 1 . 
       
     
     
         9 . The ink composition of  claim 1 , wherein
 a molecular weight of the luminescent host material is 2,000 grams per mole or less.   
     
     
         10 . The ink composition of  claim 1 , wherein
 the aromatic ether comprises a compound represented by Formula (4), the aromatic ester comprises a compound represented by Formula (5), and the aromatic ketone comprises a compound represented by Formula (6):   
       
         
           
           
               
               
           
         
         wherein, in Formula (4), X 1  is a C 1 -C 6  alkyl group, and X 2  is a hydrogen atom, a methyl group, an ethyl group, or a propyl group, 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (5), Y 1  is a C 1 -C 3  alkyl group, and Y 2  is a hydrogen atom, a methyl group, or an ethyl group, and 
       
       
         
           
           
               
               
           
         
         wherein, in Formula (6), Z 1  is a C 1 -C 4  alkyl group, and Z 2  is a hydrogen atom, a methyl group, or an ethyl group. 
       
     
     
         11 . The ink composition of  claim 1 , wherein
 the solvent comprises two or more different compounds selected from an aromatic ether, an aromatic ester, and an aromatic ketone.   
     
     
         12 . The ink composition of  claim 1 , wherein
 the solvent comprises at least one of an aromatic ether and an aromatic ester.   
     
     
         13 . The ink composition of  claim 1 , wherein
 a vapor pressure of the solvent is 1 millimeter of mercury or less.   
     
     
         14 . The ink composition of  claim 1 , further comprising a phosphorescent dopant or a fluorescent dopant. 
     
     
         15 . The ink composition of  claim 1 , wherein
 the ink composition is an ink composition for inkjet printing.   
     
     
         16 . An organic light-emitting device comprising:
 an anode;   an emission layer; and   a cathode,   wherein the emission layer is an organic film formed by using the ink composition of  claim 1 ,   wherein the emission layer comprises a luminescent host material, and   wherein the luminescent host material comprises at least one compound represented by Formula (1).   
     
     
         17 . The organic light-emitting device of  claim 16 , wherein
 the emission layer further comprises a phosphorescent dopant or a fluorescent dopant.   
     
     
         18 . A method of manufacturing an organic light-emitting device, the method comprising:
 forming an anode on a substrate;   forming an emission layer comprising the luminescent host material by coating the ink composition of  claim 1  on the anode and drying the obtained coating film; and   forming a cathode on the emission layer.   
     
     
         19 . The method of  claim 18 , wherein
 the coating of the ink composition on the anode is performed by inkjet printing.