Host materials for electroluminescent devices
A compound of Formula I wherein at least one of R 1 or R 2 includes a polycyclic group selected from the group consisting of Formula A, Formula B, and Formula C: wherein X 1 , X 2 , X 3 , and X 4 are independently CR A or N; X 5 , X 6 , X 7 , and X 8 are independently CR B or N; X 9 , X 10 , X 11 , and X 12 are independently CR C or N; X 13 , X 14 , X 15 , and X 16 are independently CR D or N; X 17 , X 18 , X 19 , and X 20 are independently CR E or N; X 21 , X 22 , X 23 , and X 24 are independently CR F or N; X 25 , X 26 , X 27 , and X 28 are independently CR G or N; X 29 , X 30 , X 31 , and X 32 are independently CR H or N; Y is selected from the group consisting of O, S, NR, and CRR′; the maximum number of N atoms that can connect to each other within each ring is two; with the proviso that R 1 does not connect to ring B, and R 2 does not connect to ring A, and wherein at least one of R C and R D of Formula A is a direct bond or an organic linker, one of R E and R F of Formula B is a direct bond or an organic linker, or one of R G , R H , and R N of Formula C is a direct bond or an organic linker.
1. A compound of Formula I
wherein at least one of R 1 or R 2 includes a polycyclic group selected from the group consisting of Formula A, Formula B, and Formula C:
wherein
X 1 , X 2 , X 3 , and X 4 are independently CR A or N;
X 5 , X 6 , X 7 , and X 8 are independently CR B or N;
X 9 , X 10 , X 11 , and X 12 are independently CR C or N;
X 13 , X 14 , X 15 , and X 16 are independently CR D or N;
X 17 , X 18 , X 19 , and X 20 are independently CR E or N;
X 21 , X 22 , X 23 , and X 24 are independently CR F or N;
X 25 , X 26 , X 27 , and X 28 are independently CR G or N;
X 29 , X 30 , X 31 , and X 32 are independently CR H or N;
Y is selected from the group consisting of O, S, NR, and CRR′;
the maximum number of N atoms that can connect to each other within each ring is two;
each R A and R B are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents R A or R B are optionally joined to form a fused ring;
R N is selected from the group consisting of a direct bond, an organic linker, hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, acyl, and combinations thereof; or optionally, R N can join with a carbon of X 9 to from a ring in Formula A, or R N can join with a carbon of X 25 to from a ring in Formula C;
R 1 and R 2 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R and R′ are each independently an aryl group;
each R C , R D , R E , R F , R G , and R H is independently a direct bond, an organic linker, a hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two substituents R C , R D , R E , R F , R G , and R H can optionally join to form a ring; and
with the proviso that R 1 does not connect to ring B, and R 2 does not connect to ring A, and wherein at least one of R C and R D of Formula A is a direct bond or an organic linker, one of R E and R F of Formula B is a direct bond or an organic linker, or one of R G , R H , and R N of Formula C is a direct bond or an organic linker.
2. The compound of claim 1 , wherein each R A and R B is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.
3. The compound of claim 1 , wherein both R 1 and R 2 is a polycyclic group independently selected from the group consisting of Formula A, Formula B, and Formula C.
4. The compound of claim 1 , wherein Y is selected from the group consisting of O and S.
5. The compound of claim 1 , wherein one of R C or R D of Formula A, one of R E or R F of Formula B, or one of R G or R H of Formula C is a direct bond to the ring A carbon of R 1 , or a direct bond to the ring B carbon of R 2 .
6. The compound of claim 1 , wherein one of R C or R D of Formula A, one of R E or R F of Formula B, or one of R G or R H of Formula C is an organic linker that connects Formula I to Formula A, Formula I to Formula B, and Formula I to Formula C, respectively, wherein the organic linker is selected from the group consisting of a C 1 -C 6 alkylene, C 2 -C 6 alkenylene, an C 2 -C 6 alkynlene, a C 5 -C 14 arylene with 0 to 3 heteroatoms, amino, silyl, —C(O)—, —S(O) 2 —, and combinations thereof.
7. The compound of claim 1 , wherein two adjacent R A join to form a fused ring, and/or two adjacent R B join to form a fused ring, wherein the fused ring is selected from the group consisting of benzene, naphthalene, pyridine, pyrimidine, imidazole, pyrrole, furan, thiophene, and any combination thereof.
8. The compound of claim 1 , wherein one of R 1 or R 2 is a heteroaryl selected from the group consisting of a carbazole or an aza-analog thereof, each of which is optionally substituted with a group R cz selected from the polycyclic group selected from the group consisting of Formula A, Formula B, or Formula C, or a group selected from the group consisting of deuterium, halogen, alkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, nitrile, sulfanyl, and combinations thereof.
9. The compound of claim 1 , wherein X 1 , X 2 , X 3 , and X 4 are CR A , and X 5 , X 6 , X 7 , and X 8 are CR B .
10. The compound of claim 1 , wherein in Formula A, X 9 , X 10 , X 11 , and X 12 are independently CR C and X 13 , X 14 , X 15 , and X 16 are independently CR D , in Formula B, X 17 , X 18 , X 19 , and X 20 are independently CR E and X 21 , X 22 , X 23 , and X 24 are independently CR F , and in Formula C, X 25 , X 26 , X 27 , and X 28 are independently CR G and X 29 , X 30 , X 31 , and X 32 are independently CR H .
11. The compound of claim 1 , wherein the organic linker is carbazole.
12. The compound of claim 1 , wherein only one of X 1 , X 2 , X 3 , and X 4 is N, and the remaining X 1 , X 2 , X 3 , and X 4 are CR A .
13. The compound of claim 1 selected from the group consisting of
14. An organic light emitting device (OLED) that includes an anode, a cathode, and
an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of Formula I
wherein at least one of R 1 or R 2 includes a polycyclic group selected from the group consisting of Formula A, Formula B, and Formula C:
wherein
X 1 , X 2 , X 3 , and X 4 are independently CR A or N;
X 5 , X 6 , X 7 , and X 8 are independently CR B or N;
X 9 , X 10 , X 11 , and X 12 are independently CR C or N;
X 13 , X 14 , X 15 , and X 16 are independently CR D or N;
X 17 , X 18 , X 19 , and X 20 are independently CR E or N;
X 21 , X 22 , X 23 , and X 24 are independently CR F or N;
X 25 , X 26 , X 27 , and X 28 are independently CR G or N;
X 29 , X 30 , X 31 , and X 32 are independently CR H or N;
Y is selected from the group consisting of O, S, NR, and CRR′;
the maximum number of N atoms that can connect to each other within each ring is two;
each R A and R B are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents R A or R B are optionally joined to form a fused ring;
R N is selected from the group consisting of a direct bond, an organic linker, hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, acyl, and combinations thereof; or optionally, R N can join with a carbon of X 9 to from a ring in Formula A, or R N can join with a carbon of X 25 to from a ring in Formula C;
R 1 and R 2 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R and R′ are each independently an aryl group;
each R C , R D , R E , R F , R G , and R H is independently a direct bond, an organic linker, a hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two substituents R C , R D , R E , R F , R G , and R H can optionally join to form a ring; and
with the proviso that R 1 does not connect to ring B, and R 2 does not connect to ring A, and wherein at least one of R C and R D of Formula A is a direct bond or an organic linker, one of R E and R F of Formula B is a direct bond or an organic linker, or one of R G , R H , and R N of Formula C is a direct bond or an organic linker.
15. The OLED of claim 14 , wherein the organic layer further comprises a light-emitting dopant that includes at least one ligand selected from the group consisting of
wherein
Y 1 to Y 13 are independently selected from carbon or nitrogen; and Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
wherein R e and R f optionally join to form a ring;
R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
each R a , R b , R c , R d , R e and R f is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents R a , R b , R c , and R d are optionally joined to form a ring, or joined to form a multidentate ligand.
16. The OLED of claim 14 , wherein the organic layer further comprises a co-host compound, wherein the co-host compound comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, triazine, pyrimidine, pyridine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole and aza-dibenzoselenophene.
17. A consumer product comprising an organic light-emitting device (OLED) that includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound of Formula I
wherein at least one of R 1 or R 2 includes a polycyclic group selected from the group consisting of Formula A, Formula B, and Formula C:
wherein
X 1 , X 2 , X 3 , and X 4 are independently CR A or N;
X 5 , X 6 , X 7 , and X 8 are independently CR B or N;
X 9 , X 10 , X 11 , and X 12 are independently CR C or N;
X 13 , X 14 , X 15 , and X 16 are independently CR D or N;
X 17 , X 18 , X 19 , and X 20 are independently CR E or N;
X 21 , X 22 , X 23 , and X 24 are independently CR F or N;
X 25 , X 26 , X 27 , and X 28 are independently CR G or N;
X 29 , X 30 , X 31 , and X 32 are independently CR H or N;
Y is selected from the group consisting of O, S, NR, and CRR′;
the maximum number of N atoms that can connect to each other within each ring is two;
each R A and R B are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two adjacent substituents R A or R B are optionally joined to form a fused ring;
R N is selected from the group consisting of a direct bond, an organic linker, hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkenyl, cycloalkenyl, aryl, heteroaryl, acyl, and combinations thereof; or optionally, R N can join with a carbon of X 9 to from a ring in Formula A, or R N can join with a carbon of X 25 to from a ring in Formula C;
R 1 and R 2 are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R and R′ are each independently an aryl group;
each R C , R D , R E , R F , R G , and R H is independently a direct bond, an organic linker, a hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and any two substituents R C , R D , R E , R F , R G , and R H can optionally join to form a ring; and
with the proviso that R 1 does not connect to ring B, and R 2 does not connect to ring A, and wherein at least one of R C and R D of Formula A is a direct bond or an organic linker, one of R E and R F of Formula B is a direct bond or an organic linker, or one of R G , R H , and R N of Formula C is a direct bond or an organic linker.
18. The consumer product of claim 17 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, a light therapy device, and a sign.
19. A formulation comprising a compound of claim 1 .
20. A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises a compound according to claim 1 or a monovalent or polyvalent variant thereof.