IP Library Granted Patent US 12,281,248
Granted Patent B2
US 12,281,248 · App. 17/296,347 · Granted Apr 22, 2025

Organic light-emitting element using polycyclic aromatic derivative compound

Inventors: Sung-hoon Joo (Cheongju-si, KR); Byung-sun Yang (Cheongju-si, KR); Su-jin Kim (Cheongju-si, KR); Ji-hwan Kim (Cheongju-si, KR); Hyeon-jun Jo (Cheongju-si, KR); Sung-eun Choi (Cheongju-si, KR); Bong-ki Shin (Cheongju-si, KR); Young-hwan Park (Cheongju-si, KR); Shuichi Hayashi (Tokyo, JP); Takeshi Yamamoto (Tokyo, JP); Shunji Mochizuki (Tokyo, JP); Yuta Hirayama (Tokyo, JP)
Assignees: SFC CO., LTD.; HODOGAYA CHEMICAL CO., LTD.
C09K11/06C07F5/02C07F5/027C07F11/00H10K85/322H10K85/626H10K85/633H10K85/636H10K85/6572H10K85/6574H10K85/6576H10K85/658C07B2200/05C09K2211/1018C09K2211/1022H10K50/15H10K50/16H10K50/171H10K50/844
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Quick Facts
Patent No.
US 12,281,248
App. No.
17/296,347
Granted
Apr 22, 2025
Kind
B2
Abstract

An organic light-emitting element according to the present invention employs a polycyclic aromatic derivative compound in a light-emitting layer inside the element, and further comprises a capping layer. Thus, the organic light-emitting element can be made highly efficient and can be useful for a device selected from among a flat panel display device, a flexible display device, a monochrome or white flat panel lighting device, and a monochrome or white flexible lighting device.

Claims (39)

1. An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, a light emitting layer interposed between the first and second electrodes, and a capping layer formed on one of the surfaces of the first and second electrodes opposite to the light emitting layer, wherein the light emitting layer comprises a compound represented by Formula A-5 and the capping layer comprises a compound represented by Formula B:

wherein each Z is independently CR or N, Y 1 and Y 2 are identical to or different from each other and are each independently selected from the group consisting of CR 2 R 3 , O, S, Se, and SiR 4 R 5 , Y 3 and Y 4 are identical to or different from each other and are each independently selected from the group consisting of CR 2 R 3 , and SiR 4 R 5 , X is selected from the group consisting of B, P, P═S, and P═O, and R, R 2 to R 5 are identical to or different from each other and are independently selected from the group consisting of 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 R are optionally bonded to each other or are optionally linked to other adjacent R to form alicyclic or aromatic monocyclic or polycyclic rings whose carbon atoms are optionally substituted with one or more heteroatoms selected from the group consisting of N, S, and O atoms, and

wherein R 41 to R 43 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 the group consisting of 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.

2. The organic electroluminescent device according to claim 1 , wherein at least one of Ar 31 to Ar 34 in Formula B is represented by Formula C:

wherein R 51 to R 54 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 , or 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 B.

3. The organic electroluminescent device according to claim 1 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B1 to B79:

4. The organic electroluminescent device according to claim 1 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B101 to B145:

5. The organic electroluminescent device according to claim 1 , wherein the light emitting layer comprises, as a host compound, an anthracene derivative represented by Formula D:

wherein R 21 to R 28 are identical to or different from each other and are as defined for R, R 2 to R 5 in Formula A-5, Ar 9 and Ar 10 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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.

6. The organic electroluminescent device according to claim 5 , wherein the compound of Formula D is selected from the group consisting of the compounds of Formulae D1 to D48:

7. The organic electroluminescent device according to claim 1 , further comprising a hole transport layer and an electron blocking layer interposed between the first electrode and the second electrode wherein each of the hole transport layer and the electron blocking layer comprises a compound represented by Formula E:

wherein R 61 to R 63 are identical to or different from each other and are each independently selected from the group consisting of 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.

8. The organic electroluminescent device according to claim 7 , wherein the compound of Formula E is selected from the group consisting of the compounds of Formulae E1 to E33:

9. The organic electroluminescent device according to claim 1 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B101 to B145:

10. An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, a light emitting layer interposed between the first and second electrodes, and a capping layer formed on one of the surfaces of the first and second electrodes opposite to the light emitting layer, wherein the light emitting layer comprises any one of compounds represented by Formula A-4 or Formula A-6 and the capping layer comprises a compound represented by Formula B:

wherein each Z is independently CR or N, Y 1 and Y 2 are identical to or different from each other and are each independently selected from the group consisting of CR 2 R 3 , O, S, Se, and SiR 4 R 5 , Y 3 and Y 4 are identical to or different from each other and are each independently selected from the group consisting of CR 2 R 3 , and SiR 4 R 5 , and X is selected from the group consisting of B, P, P═S, and P═O, and R, R 2 to R 5 are identical to or different from each other and are independently selected from the group consisting of 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 R are optionally bonded to each other or are optionally linked to other adjacent R to form alicyclic or aromatic monocyclic or polycyclic rings whose carbon atoms are optionally substituted with one or more heteroatoms selected from the group consisting of N, S, and O atoms, and

wherein R 41 to R 43 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 the group consisting of 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 5 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.

11. The organic electroluminescent device according to claim 10 , wherein at least one of Ar 31 to Ar 34 in Formula B is represented by Formula C:

wherein R 51 to R 54 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 , or 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 B.

12. The organic electroluminescent device according to claim 10 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B1 to B79:

13. The organic electroluminescent device according to claim 10 , wherein the light emitting layer comprises, as a host compound, an anthracene derivative represented by Formula D:

wherein R 21 to R 28 are identical to or different from each other and are as defined for R, R 2 to R 5 in Formula A-4 or A-6, Ar 9 and Ar 10 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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.

14. The organic electroluminescent device according to claim 13 , wherein the compound of Formula D is selected from the group consisting of the compounds of Formulae D1 to D48:

15. The organic electroluminescent device according to claim 10 , further comprising a hole transport layer and an electron blocking layer interposed between the first electrode and the second electrode wherein each of the hole transport layer and the electron blocking layer comprises a compound represented by Formula E:

wherein R 61 to R 63 are identical to or different from each other and are each independently selected from the group consisting of 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.

16. The organic electroluminescent device according to claim 15 , wherein the compound of Formula E is selected from the group consisting of the compounds of Formulae E1 to E33:

17. An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, a light emitting layer interposed between the first and second electrodes, and a capping layer formed on one of the surfaces of the first and second electrodes opposite to the light emitting layer, wherein the light emitting layer comprises a compound represented by Formula A-3 and the capping layer comprises a compound represented by Formula B:

wherein each Z is independently CR or N, Y are identical to or different from each other and are each independently selected from the group consisting of CR 2 R 3 , Se, and SiR 4 R 5 , X is selected from the group consisting of B, P, P═S, and P═O, and R, R 2 to R 5 are identical to or different from each other and are independently selected from the group consisting of 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 R are optionally bonded to each other or are optionally linked to other adjacent R to form alicyclic or aromatic monocyclic or polycyclic rings whose carbon atoms are optionally substituted with one or more heteroatoms selected from the group consisting of N, S, and O atoms, and

wherein R 41 to R 43 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 the group consisting of 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.

18. The organic electroluminescent device according to claim 17 , wherein at least one of Ar 31 to Ar 34 in Formula B is represented by Formula C:

wherein R 51 to R 54 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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 , or 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 B.

19. The organic electroluminescent device according to claim 17 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B1 to B79:

20. The organic electroluminescent device according to claim 17 , wherein the compound of Formula B is selected from the group consisting of the following the compounds of Formula B101 to B145:

21. The organic electroluminescent device according to claim 17 , wherein the light emitting layer comprises, as a host compound, an anthracene derivative represented by Formula D:

wherein R 21 to R 28 are identical to or different from each other and are as defined for R, R 2 to R 5 in Formula A-3 or A-5, Ar 9 and Ar 10 are identical to or different from each other and are each independently selected from the group consisting of 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 the group consisting of 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.

22. The organic electroluminescent device according to claim 21 , wherein the compound of Formula D is selected from the group consisting of the compounds of Formulae D1 to D48:

23. The organic electroluminescent device according to claim 17 , further comprising a hole transport layer and an electron blocking layer interposed between the first electrode and the second electrode wherein each of the hole transport layer and the electron blocking layer comprises a compound represented by Formula E:

wherein R 61 to R 63 are identical to or different from each other and are each independently selected from the group consisting of 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.

24. The organic electroluminescent device according to claim 23 , wherein the compound of Formula E is selected from the group consisting of the compounds of Formulae E1 to E33:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2021
From: JOO, SUNG-HOON; YANG, BYUNG-SUN; KIM, SU-JIN; KIM, JI-HWAN; JO, HYEON-JUN; CHOI, SUNG-EUN; SHIN, BONG-KI; PARK, YOUNG-HWAN; HAYASHI, SHUICHI; YAMAMOTO, TAKESHI; MOCHIZUKI, SHUNJI; HIRAYAMA, YUTA
To: SFC CO., LTD.; HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 056329/0467 →
Priority Claims (2)
KR 10-2018-0151781 · Nov 30, 2018 · national
KR 10-2019-0154524 · Nov 27, 2019 · national
Continuity (1)
Related Publication 20220102635A1 · Mar 31, 2022
References Cited (59)
US 20030137239A1 · Matsuura et al. · 2003 [cited by applicant]
US 20040217934A1 · Yang · 2004 [cited by applicant]
US 20060043858A1 · Ikeda · 2006 [cited by examiner]
US 20090053557A1 · Spindler et al. · 2009 [cited by applicant]
US 20140225100A1 · Yokoyama · 2014 [cited by examiner]
US 20150236274A1 · Hatakeyama · 2015 [cited by examiner]
US 20160056386A1 · Lee et al. · 2016 [cited by applicant]
US 20170213969A1 · Shin et al. · 2017 [cited by applicant]
US 20170346009A1 · Yokoyama · 2017 [cited by examiner]
US 20180006235A1 · Yokoyama et al. · 2018 [cited by applicant]
US 20180301629A1 · Hatakeyama et al. · 2018 [cited by applicant]
US 20190207112A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20200098991A1 · Kim et al. · 2020 [cited by applicant]
US 20200176679A1 · Jeong et al. · 2020 [cited by applicant]
US 20210184121A1 · Suh · 2021 [cited by examiner]
CN 101490207A · 2009 [cited by applicant]
CN 103864789A · 2014 [cited by applicant]
CN 107342366A · 2017 [cited by applicant]
CN 107851724A · 2018 [cited by applicant]
CN 107925001A · 2018 [cited by applicant]
EP 3246963A2 · 2017 [cited by applicant]
EP 3660024A1 · 2020 [cited by applicant]
JP 201472120A · 2014 [cited by applicant]
JP 201686147A · 2016 [cited by applicant]
JP 2017168796A · 2017 [cited by applicant]
JP 6755806B2 · 2020 [cited by applicant]
JP 2021504373A · 2021 [cited by applicant]
KR 1020160087059A · 2016 [cited by applicant]
KR 1020170061772A · 2017 [cited by applicant]
KR 1020170089094A · 2017 [cited by applicant]
KR 1020170127593A · 2017 [cited by applicant]
KR 1020170130434A · 2017 [cited by applicant]
KR 1020170130435A · 2017 [cited by applicant]
KR 1020180018404A · 2018 [cited by applicant]
KR 1020180037695A · 2018 [cited by applicant]
KR 101876763B1 · 2018 [cited by applicant]
KR 1020180122298A · 2018 [cited by applicant]
KR 1020190128954A · 2019 [cited by applicant]
KR 102094830B1 · 2020 [cited by applicant]
WO WO2015001726A1 · 2015 [cited by examiner]
WO WO2016104289A1 · 2016 [cited by examiner]
WO WO2017027333A1 · 2017 [cited by applicant]
WO WO2017183625A1 · 2017 [cited by applicant]
WO WO2018095397A1 · 2018 [cited by applicant]
WO WO2018203666A1 · 2018 [cited by applicant]
WO WO2020054676A1 · 2020 [cited by applicant]
Englsih language translation of WO 2015001726A1, Apr. 19, 2023, pp. 1-24. [cited by examiner]
International Search Report issued on Mar. 20, 2020 in counterpart International Patent Application No. PCT/KR2019/016612 (2 pages in English and 2 pages in Korean). [cited by applicant]
Japanese Office Action issued on Jun. 21, 2022, in counterpart Japanese Patent Application No. 2021-531137 (4 pages in Japanese). [cited by applicant]
Extended European search report issued on Aug. 10, 2022, in counterpart European Patent Application No. 19890930.1 (8 pages in English). [cited by applicant]
Chinese Office Action issued on Apr. 22, 2023, in corresponding Chinese Patent Application No. 201980078604.9 (9 pages in English, 8 pages in Chinese). [cited by applicant]
Chinese Office Action issued on Sep. 18, 2020, in corresponding Chinese Patent Application No. 201911199295.9 (12 pages in English, 7 pages in Chinese). [cited by applicant]
Japanese Office Action issued on Aug. 25, 2020, in corresponding Japanese Patent Application No. 2019-217554 (4 pages in Japanese). [cited by applicant]
Korean Office Action issued on Dec. 24, 2019, in corresponding Korean Patent Application No. 10-2019-0069314 (3 pages in Korean). [cited by applicant]
United States Office Action issued on Aug. 19, 2020, in U.S. Appl. No. 16/687,916 (16 pages in English). [cited by applicant]
Liang, Xiao, et al. “Peripheral amplification of multi-resonance induced thermally activated delayed fluorescence for highly efficient OLEDs.” [cited by applicant]
Saito, Shohei, et al., “Polycyclic π-electron System with Boron at Its Center.” Journal of the American Chemical Society 134.22 (2012): 9130-9133. [cited by applicant]
Korean Office Action issued on Oct. 10, 2019, in counterpart Korean Patent Application No. 10-2019-0069314 (3 pages in English, 3 pages in Korean). [cited by applicant]
Korean Office Action issued on Dec. 24, 2019, in counterpart Korean Patent Application No. 10-2019-0069314 (2 pages in English, 2 pages in Korean). [cited by applicant]
Cited By (1)
US 12,552,984