Organic electroluminescent device
Disclosed is an organic electroluminescent device that employs a compound represented by Formula A-1 or A-2: and a compound represented by Formula B: The organic electroluminescent device has excellent luminescent properties such as high color purity and long lifetime.
1 . An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and a light emitting layer interposed between the first and second electrodes wherein the light emitting layer comprises a compound represented by Formula A-1 or A-2:
wherein Q 1 to Q 3 are identical to or different from each other and are each independently a substituted or unsubstituted C 6 -C 50 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 -C 50 heteroaromatic ring;
wherein the linker Y 1 is selected from N—R 1 , CR 2 R 3 , Se, and SiR 4 R 5 , and R 1 to R 5 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that each of R 1 to R 5 is optionally bonded to Q 1 to form an alicyclic or aromatic monocyclic or polycyclic ring, R 2 and R 3 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R 4 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring;
wherein the linkers Y 2 and Y 3 are identical to or different from each other and are each independently selected from N—R 1 , CR 2 R 3 , Se, and SiR 4 R 5 , X is selected from B, P, and P═O, and R 1 to R 5 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that each of R 1 to R 5 is optionally bonded to Q 2 or Q 3 to form an alicyclic or aromatic monocyclic or polycyclic ring, R 2 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R 4 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring;
wherein Q 1 , Q 2 , Q 3 , X, and Y 1 to Y 3 are as defined in Formula A-1; and
an anthracene derivative represented by Formula B:
wherein R 1 to R 5 are each independently hydrogen, deuterium or C 6 -C 24 aryl and R 6 to R 22 are each independently hydrogen or deuterium, and
wherein the compound of Formula A-1 or A-2 has a structure represented by Formula A-3 or A-4:
wherein each Z is independently CR or N, the substituents R are identical to or different from each other and are independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that the substituents R are optionally bonded to each other or are optionally linked to other adjacent substituents to form alicyclic or aromatic monocyclic or polycyclic rings whose carbon atoms are optionally substituted with one or more heteroatoms selected from N, S, and O atoms, and X and Y 1 to Y 3 are as defined in Formulae A-1 and A-2,
wherein X, Y 1 to Y 3 , and Z are as defined in Formula A-3, and
wherein the compound represented by Formula B is selected from the compounds of Formulae B2 to B16:
2 . The organic electroluminescent device according to claim 1 , wherein at least one of R 6 to R 13 in Formula B is deuterium.
3 . The organic electroluminescent device according to claim 1 , wherein at least one of R 1 to R 5 in Formula B is deuterium and at least one of R 6 to R 13 in Formula B is deuterium.
4 . The organic electroluminescent device according to claim 1 , wherein the light emitting layer further comprises, as a host compound, an anthracene derivative represented by Formula C:
wherein R 21 to R 28 are identical to or different from each other and are as defined for R 1 to R 4 in Formula A-1 or A-2, Ar 9 and Ar 10 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 2 -C 30 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 5 -C 30 cycloalkenyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 2 -C 30 heterocycloalkyl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 6 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 6 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, and substituted or unsubstituted C 6 -C 30 arylsilyl, L 13 is a single bond or is selected from substituted or unsubstituted C 6 -C 20 arylene and substituted or unsubstituted C 2 -C 20 heteroarylene, and k is an integer from 1 to 3, provided that when k is 2 or more, the linkers L 13 are identical to or different from each other.
5 . The organic electroluminescent device according to claim 4 , wherein Ar 9 in Formula C is represented by Formula C-1:
wherein R 31 to R 35 are identical to or different from each other and are as defined for R 1 to R 4 in Formula A, and each of R 31 to R 35 is optionally bonded to an adjacent substituent to form a saturated or unsaturated ring.
6 . The organic electroluminescent device according to claim 4 , wherein compound of Formula C is selected from the compounds of Formulae C1 to C48:
7 . The organic electroluminescent device according to claim 1 , further comprising a hole transport layer, an electron blocking layer, and a capping layer, each of which comprises a compound represented by Formula D:
wherein R 41 to R 43 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 7 -C 50 arylalkyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 6 -C 30 arylsilyl, and halogen, L 31 to L 34 are identical to or different from each other and are each independently single bonds or selected from substituted or unsubstituted C 6 -C 50 arylene and substituted or unsubstituted C 2 -C 50 heteroarylene, Ar 31 to Ar 34 are identical to or different from each other and are each independently selected from substituted or unsubstituted C 6 -C 50 aryl and substituted or unsubstituted C 2 -C 50 heteroaryl, n is an integer from 0 to 4, provided that when n is 2 or greater, the aromatic rings containing R 43 are identical to or different from each other, m 1 to m 3 are integers from 0 to 4, provided that when both m 1 and m 3 are 2 or more, the R 41 , R 42 , and R 43 groups are identical to or different from each other, and hydrogen or deuterium atoms are bonded to the carbon atoms of the aromatic rings to which R 41 to R 43 are not attached.
8 . The organic electroluminescent device according to claim 7 , wherein at least one of Ar 31 to Ar 34 is represented by Formula E:
wherein R 51 to R 54 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 2 -C 30 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 5 -C 30 cycloalkenyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 2 -C 30 heterocycloalkyl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, which are optionally linked to each other to form a ring, Y is a carbon or nitrogen atom, Z is a carbon, oxygen, sulfur or nitrogen atom, Ar 35 to Ar 37 are identical to or different from each other and are each independently selected from substituted or unsubstituted C 5 -C 50 aryl and substituted or unsubstituted C 3 -C 50 heteroaryl, provided that when Z is an oxygen or sulfur atom, Ar 37 is nothing, provided that when Y and Z are nitrogen atoms, only one of Ar 35 , Ar 36 , and Ar 37 is present, provided that when Y is a nitrogen atom and Z is a carbon atom, Ar 36 is nothing, with the proviso that one of R 51 to R 54 and Ar 35 to Ar 37 is a single bond linked to one of the linkers L 31 to L 34 in Formula D.
9 . The organic electroluminescent device according to claim 7 , wherein the compound of Formula D is selected from the compounds of Formulae D1 to D79:
10 . The organic electroluminescent device according to claim 7 , wherein the compound of Formula D is selected from the compounds of Formulae D101 to D145:
11 . The organic electroluminescent device according to claim 1 , further comprising a hole transport layer, an electron blocking layer, and a capping layer, each of which comprises a compound represented by Formula F:
wherein R 61 to R 63 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 2 -C 30 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 5 -C 30 cycloalkenyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 2 -C 30 heterocycloalkyl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 6 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 6 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 6 -C 30 arylsilyl, substituted or unsubstituted C 1 -C 30 alkylgermanium, substituted or unsubstituted C 1 -C 30 arylgermanium, cyano, nitro, and halogen, and Ar 51 to Ar 54 are identical to or different from each other and are each independently substituted or unsubstituted C 6 -C 40 aryl or substituted or unsubstituted C 2 -C 30 heteroaryl.
12 . The organic electroluminescent device according to claim 11 , wherein the compound of Formula F is selected from the compounds of Formulae F1 to F33:
13 . An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and a light emitting layer interposed between the first and second electrodes wherein the light emitting layer comprises a compound represented by Formula A-1 or A-2:
wherein Q 1 to Q 3 are identical to or different from each other and are each independently a substituted or unsubstituted C 6 -C 50 aromatic hydrocarbon ring or a substituted or unsubstituted C 2 -C 50 heteroaromatic ring;
wherein the linker Y 1 is selected from N—R 1 , CR 2 R 3 , Se, and SiR 4 R 5 , and R 1 to R 5 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that each of R 1 to R 5 is optionally bonded to Q 1 to form an alicyclic or aromatic monocyclic or polycyclic ring, R 2 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R 4 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring;
wherein the linkers Y 2 and Y 3 are identical to or different from each other and are each independently selected from N—R 1 , CR 2 R 3 , Se, and SiR 4 R 5 , X is selected from B, P, and P═O, and R 1 to R 5 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that each of R 1 to R 5 is optionally bonded to Q 2 or Q 3 to form an alicyclic or aromatic monocyclic or polycyclic ring, R 2 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R 4 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring;
wherein Q 1 , Q 2 , Q 3 , X, and Y 1 to Y 3 are as defined in Formula A-1; and an anthracene derivative represented by Formula B:
wherein R 1 to R 5 are each independently hydrogen, deuterium or C 6 -C 24 aryl and Re to R 22 are each independently hydrogen or deuterium, and
wherein the compound of Formula A-1 or A-2 has a structure represented by Formula A-5 or A-6:
wherein each Z is independently CR or N, the substituents R are identical to or different from each other and are independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that the substituents R are optionally bonded to each other or are optionally linked to other adjacent substituents to form alicyclic or aromatic monocyclic or polycyclic rings whose carbon atoms are optionally substituted with one or more heteroatoms selected from N, S, and O atoms, and X and Y 1 to Y 3 are as defined in Formulae A-1 and A-2, wherein the linker Y 4 is selected from N—R 1 , CR 2 R 3 , Se, and SiR 4 R 5 , and R 1 to R 5 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 30 alkyl, substituted or unsubstituted C 6 -C 50 aryl, substituted or unsubstituted C 3 -C 30 cycloalkyl, substituted or unsubstituted C 2 -C 50 heteroaryl, substituted or unsubstituted C 1 -C 30 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 1 -C 30 alkylthioxy, substituted or unsubstituted C 5 -C 30 arylthioxy, substituted or unsubstituted C 1 -C 30 alkylamine, substituted or unsubstituted C 5 -C 30 arylamine, substituted or unsubstituted C 1 -C 30 alkylsilyl, substituted or unsubstituted C 5 -C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that each of R 1 to R 5 is optionally bonded to Q 1 to form an alicyclic or aromatic monocyclic or polycyclic ring, R 2 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R 4 and R 5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring;
wherein X, Y 1 to Y 4 , and Z are as defined in Formula A-5, and
wherein the compound represented by Formula B is selected from the compounds of Formulae B2 to B16:
14 . The organic electroluminescent device according to claim 13 , wherein at least one of R 6 to R 13 in Formula B is deuterium.
15 . The organic electroluminescent device according to claim 13 , wherein at least one of R 1 to R 5 in Formula B is deuterium and at least one of R 6 to R 13 in Formula B is deuterium.
16 . An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and a light emitting layer interposed between the first and second electrodes wherein the light emitting layer comprises a compound selected from the compounds of Formulae A3, A4, A7 to A9, A14, A15, A17 to A105, A107 to A116, and A118 to A176:
and and an anthracene derivative represented by Formula B:
wherein R 1 to R 5 are each independently hydrogen, deuterium or C 6 -C 24 aryl and R 6 to R 22 are each independently hydrogen or deuterium, and
wherein the compound represented by Formula B is selected from the compounds of Formulae B2 to B16:
17 . The organic electroluminescent device according to claim 16 , wherein at least one of Re to R 13 in Formula B is deuterium.
18 . The organic electroluminescent device according to claim 16 , wherein at least one of R 1 to R 5 in Formula B is deuterium and at least one of R 6 to R 13 in Formula B is deuterium.