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US 2024/0190901 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsTyler FLEETHAM, Bin MA, Fadi M. JRADI, Elena SHEINA, Siva Kumar TALLURI, Noah HORWITZ, Mahesh PAUDYAL
Life of this patent
Estimating the term…
Abstract
Provided are compounds comprising as a central moiety a 6-membered aromatic ring which is fused to a 5-membered heterocyclic ring comprising at least two nitrogen atoms. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) as well as related consumer products that utilize these compounds.
Claims20
A compound of Formula I:
- wherein X0 is C;
- X1 to X4 are each independently C or N;
- RA is mono to the maximum allowable substitution or no substitution;
- each RA and RG is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one of RA and RG is Formula II to Formula V or a substituted or unsubstituted tercarbazole,
- wherein
- X5 to X7 are each independently CRB′ or N
- X8 to X18 are each independently C or N;
- at least one of X5 to X7 is N;
- RD are each independently a substituted or unsubstituted aryl or heteroaryl group;
- RC and RD are joined together to form a 5-membered heterocyclic ring, with the proviso that RC and RD are not joined to form an indolocarbazole;
- Y1 and Y2 are each independently selected from the group consisting of O, S, Se, SiRR′, and GeRR′;
- RM, RE and RF are each mono to the maximum allowable substitution or no substitution;
- L1 is a direct bond or is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′R″, P(O)R′, SiR′R″, GeR′R″, aryl, heteroaryl, alkyl, cycloalkyl, heteroalkyl, and combinations thereof,
- each R′, R″, RB, RB′, RC, RE, RF, RM and RN is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, imino, and combinations thereof;
- with the proviso that if L1 is attached to X0 then L1 is selected from the group consisting of a direct bond, SiR′R″, GeR′R″, carbazole, phenyl, pyridine, pyrimidine, pyrazine, or triazine;
- Z is C, Si or Ge;
- L2 is a direct bond or is selected from the group consisting of carbazole, pyridine, pyrimidine, pyrazine, or triazine;
- A1 and A2 are each independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- A3 is a substituted or unsubstituted aryl or heteroaryl, with the proviso that A3 is not benzimidazole;
- any two groups may be joined or fused to form a ring with the proviso that two RA or two RE are not joined to form a 5 membered ring;
- wherein the dashed line () in each of Formulae II-V indicates the bond to the structure of Formula I;
- with the proviso that when RA is Formula V and attached to Formula I at X0, RG is not selected from the group consisting of 1-naphtyl, 2-anthryl, 3-phenanthryl, 2-pyrenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenoxyphosphoryl, diphenylphosphoryl, 3-trifluoromethylphenyl, 4-diphenylmethanoyl, 2-diphenylmethanyol, diphenylsulphonyl, dipyridoyl, benzooxazoyl, 5-quinolyl, 6-quinolyl, 2-quinoxalyl, 6-quinoxalyl, 1, 5-napthyridinyl, 1, 10-phenanthrolinyl, N-phenylbenzimidazolyl and 3-phenylquinoxalinyl;
- and
- with the proviso that the compound does not comprise a group selected from cycloalkenyl, oxazole, oxadiazole, or an uncyclized diphenyl amine, and the compound is not
22 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound of Formula I:
- wherein X0 is C;
- X1 to X4 are each independently C or N;
- RA is mono to the maximum allowable substitution or no substitution;
- each RA and RG is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one of RA and RG is Formula II to Formula V or a substituted or unsubstituted tercarbazole,
- wherein
- X5 to X7 are each independently CRB′ or N
- X8 to X18 are each independently C or N;
- at least one of X5 to X7 is N;
- RD are each independently a substituted or unsubstituted aryl or heteroaryl group;
- RC and RD are joined together to form a 5-membered heterocyclic ring, with the proviso that RC and RD are not joined to form an indolocarbazole;
- Y1 and Y2 are each independently selected from the group consisting of O, S, Se, SiRR′, and GeRR′;
- RE and RF are each mono to the maximum allowable substitution or no substitution;
- L1 is a direct bond or is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′R″, P(O)R′, SiR′R″, GeR′R″, aryl, heteroaryl, alkyl, cycloalkyl, heteroalkyl, and combinations thereof,
- each R′, R″, RB, RB′, RC, RE, RF, RM and RN is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, imino, and combinations thereof;
- with the proviso that if L1 is attached to X0 then L 1 is selected from the group consisting of a direct bond, SiR′R″, GeR′R″, carbazole, phenyl, pyridine, pyrimidine, pyrazine, or triazine;
- Z is C, Si or Ge;
- L2 is a direct bond or is selected from the group consisting of carbazole, pyridine, pyrimidine, pyrazine, or triazine;
- A1 and A2 are each independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- A3 is a substituted or unsubstituted aryl or heteroaryl, with the proviso that A3 is not benzimidazole;
- any two groups may be joined or fused to form a ring with the proviso that two RA or two RE are not joined to form a 5 membered ring;
- wherein the dashed line () in each of Formulae II-V indicates the bond to the structure of Formula I;
- with the proviso that when RA is Formula V and attached to Formula I at X0, RG is not selected from the group consisting of 1-naphthyl, 2-anthryl, 3-phenanthryl, 2-pyrenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenoxyphosphoryl, diphenylphosphoryl, 3-trifluoromethylphenyl, 4-diphenylmethanoyl, 2-diphenylmethanoyl, diphenylsulphonyl, dipyridoyl, benzoxazolyl, 5-quinolyl, 6-quinolyl, 2-quinoxalyl, 6-quinoxalyl, 1, 5-naphthyridinyl, 1, 10-phenanthrolinyl, N-phenylbenzimidazolyl and 3-phenylquinoxalinyl;
- and
- with the proviso that the compound does not comprise a group selected from cycloalkenyl, oxazole, oxadiazole, or an uncyclized diphenyl amine, and the compound is not
27 more elements
A consumer product comprising an organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound of Formula I:
- wherein X0 is C;
- X1 to X4 are each independently C or N;
- RA is mono to the maximum allowable substitution or no substitution;
- each RA and RG is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one of RA and RG is Formula 11 to Formula V or a substituted or unsubstituted tercarbazole,
- wherein
- X5 to X7 are each independently CRB′ or N
- X8 to X18 are each independently C or N;
- at least one of X5 to X7 is N;
- RD are each independently a substituted or unsubstituted aryl or heteroaryl group;
- RC and RD are joined together to form a 5-membered heterocyclic ring, with the proviso that RC and RD are not joined to form an indolocarbazole;
- Y1 and Y2 are each independently selected from the group consisting of O, S, Se, SiRR′, and GeRR′;
- RE and RF are each mono to the maximum allowable substitution or no substitution;
- L1 is a direct bond or is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, C═S, C═Se, C═NR′, C═CR′R″, S═O, SO2, CR′R″, P(O)R′, SiR′R″, GeR′R″, aryl, heteroaryl, alkyl, cycloalkyl, heteroalkyl, and combinations thereof,
- each R′, R″, RB, RB′, RC, RE, RF, RM and RN is independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, imino, and combinations thereof;
- with the proviso that if L is attached to X then L is selected from the group consisting of a direct bond, SiR′R″, GeR′R″, carbazole, phenyl, pyridine, pyrimidine, pyrazine, or triazine;
- Z is C, Si or Ge;
- L2 is a direct bond or is selected from the group consisting of carbazole, pyridine, pyrimidine, pyrazine, or triazine;
- A1 and A2 are each independently hydrogen or selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- A3 is a substituted or unsubstituted aryl or heteroaryl, with the proviso that A3 is not benzimidazole;
- any two groups may be joined or fused to form a ring with the proviso that two RA or two RE are not joined to form a 5 membered ring;
- wherein the dashed line () in each of Formulae II-V indicates the bond to the structure of Formula I;
- with the proviso that when RA is Formula V and attached to Formula I at X0, RG is not selected from the group consisting of 1-naphthyl, 2-anthryl, 3-phenanthryl, 2-pyrenyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, triphenoxyphosphoryl, diphenylphosphoryl, 3-trifluoromethylphenyl, 4-diphenylmethanol, 2-diphenylmethanol, diphenylsulphonyl, dipyridoyl, benzoxazolyl, 5-quinolyl, 6-quinolyl, 2-quinoxalyl, 6-quinoxalyl, 1, 5-naphthyridinyl, 1, 10-phenanthrolinyl, N-phenylbenzimidazolyl and 3-phenylquinoxalinyl;
- and
- with the proviso that the compound does not comprise a group selected from cycloalkenyl, oxazole, oxadiazole, or an uncyclized diphenyl amine, and the compound is not
27 more elements
Dependencies are inferred from the claim text.