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US 2022/0177492 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsTyler FLEETHAM, Nicholas J. THOMPSON, Chun LIN, Jerald FELDMAN, Peter WOLOHAN, Bin MA
Life of this patent
Estimating the term…
Abstract
Provided are new compositions of matter for host materials in OLEDs by incorporating deuterated moieties in the organic molecules. Also provided are formulations comprising these deuterated compounds. Further provided are OLEDs and related consumer products that utilize these deuterated compounds.
Claims28
A compound selected from the group consisting of Formula (1) to Formula (14) shown below:
- wherein at least one of RA, and at least one of RB is D,
- wherein at least one of RC and RD is D,
- wherein at least one of RE, RF, RG, and RH is D,
- wherein at least one of RI, RJ, and RK is D,
- wherein at least one of RL, RM, and RN is D,
- wherein at least one of RO, RP, and RQ is D,
- wherein at least one of RR and RS is D,
- wherein at least one of RT, RU, RV, and RW is D,
- wherein at least one of RX and RYis D,
- wherein at least one of RAB and RAC is D,
- wherein at least one of RAF and RAG is D,
- wherein at least one of RAL and RAM, and at least one of RAN is D,
- wherein at least one of RAT, RAU, RAV, and RAW is D, and
- wherein at least one of RAY and RAZ is D;
- wherein:
- RA to RBB each independently represents mono to the maximum allowable substitution, or no substitution;
- X1-X138 are each independently C or N;
- at least one of X1 to X8 and one of X114 to X116 is N;
- at least one of X32 and X34 is C;
- Y1 to Y5 each independently is selected from the group consisting of O, S, and Se;
- one of Y2 and Y3 can also present no bond;
- L is a direct bond or an organic linker;
- at least one of RE, RF, RG, and RH is selected from the group consisting of aryl, heteroaryl, amino, silyl, boryl, and combinations thereof;
- any two adjacent substituents of RA to RS, RAL to RAO, RAY, RAZ, RBA, and RBB can join or fuse into a ring;
- provided that any two adjacent substituents of RL, RM, and RN do not join or fuse into a indolo[3,2,1-jk]carbazole;
- each RY is H or D;
- at least one of R2 and R3 comprises a chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and boron atom;
- R8 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof,
- each RA to RAO, RAT to RBB, R1 to R7 is independently a hydrogen or the general substituents described above;
- when compound is formula (14), at least one of the following two conditions is true:
- (a) each RAP to RAS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof, at least one of RAP to RAS is unique;
- and the compound only comprises one Si;
- and
- (b) each RAP to RAS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one of RAP, one of RAQ, one of RAR, and one of RAS is deuterium;
- any two adjacent RAP to RAS can be joined or fused to form a ring;
- at least one of RAP to RAS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, biscarbazole, and combinations thereof,
- provided that each RAP to RAS does not comprises a 6-membered ring containing exact one B and exact one N;
- and
- with the proviso that the compound is not:
37 more elements
-8. (canceled)
-11. (canceled)
16-17. (canceled)
-22. (canceled)
-25. (canceled)
-29. (canceled)
-38. (canceled)
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 selected from the group consisting of Formula (1) to Formula (14) shown below:
- wherein at least one of RA, and at least one of RB is D,
- wherein at least one of RC and RD is D,
- wherein at least one of RE, RF, RG, and RH is D,
- wherein at least one of RI, RJ, and RK is D,
- wherein at least one of RL, RM, and RN is D,
- wherein at least one of RO, RP, and RQ is D,
- wherein at least one of RR and RS is D,
- wherein at least one of RT, RU, RV, and RW is D,
- wherein at least one of RX and RY is
- wherein at least one of RAB and RAC is D,
- wherein at least one of RAF and RAG is D,
- wherein at least one of RAL and RAM, and at least one of RAN is D,
- wherein at least one of RAT, RAU, RAV, and RAW is D, and
- wherein at least one of RAY and RAZ is D;
- wherein:
- RA to RBB each independently represents mono to the maximum allowable substitution, or no substitution;
- X1-X138 are each independently C or N;
- at least one of X1 to X8 and one of X114 to X116 is N;
- at least one of X32 and X34 is C;
- Y1 to Y5 each independently is selected from the group consisting of O, S, and Se;
- one of Y2 and Y3 can also present no bond;
- at least one of RE, RF, RG, and RH is selected from the group consisting of aryl, heteroaryl, amino, silyl, boryl, and combinations thereof;
- any two adjacent substituents of RA to RS, RAL to RAO, RAY, RAZ, RBA, and RBB can join or fuse into a ring;
- provided that any two adjacent substituents of RL, RM, and RN do not join or fuse into a indolo[3,2,1-jk]carbazole;
- each RY is H or D;
- at least one of R2 and R3 comprises a chemical group selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and boron atom;
- R8 is selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof,
- each RA to RAO, RAT to RBB, R1 to R7 is independently a hydrogen or the general substituents described above;
- when compound is formula (14), at least one of the following two conditions is true:
- (a) each RAP to RAS is independently selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, selenyl, and combinations thereof;
- at least one of RAP to RAS is unique;
- and the compound only comprises one Si;
- and
- (b) each RAP to RAS is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
- at least one of RAP, one of RAQ, one of RAR, and one of RAS is deuterium;
- any two adjacent RAP to RAS can be joined or fused to form a ring;
- at least one of RA to RAS comprises a group selected from the group consisting of triazine, pyrimidine, pyridine, pyrazine, boryl, silane, 5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, tetraphenylene, biscarbazole, and combinations thereof;
- provided that each RAP to RAS does not comprises a 6-membered ring containing exact one B and exact one N;
- and
- with the proviso that the compound is not:
42 more elements
-42. (canceled)
Dependencies are inferred from the claim text.