Granted Patent B2

US 12,598,913 · App. 17/514,617 · Granted Apr 7, 2026

Inventors: Guomeng Li (Kunshan, CN); Yuewei Zhang (Kunshan, CN); Jinbei Wei (Kunshan, CN); Mengzhen Li (Kunshan, CN)

Assignee: KunShan Go-Visionox Opto-Electronics Co., Ltd

H10K85/636H10K85/324H10K85/622H10K85/624H10K85/626H10K85/633H10K85/654H10K85/6572H10K85/6574H10K85/658H10K50/11H10K2101/10

Abstract

Claims (46)

1 . An organic light emitting device, comprising a light-emitting layer, wherein the light-emitting layer comprises a host material and a dye, the host material is a triplet-triplet annihilation material, and the dye is a boron-nitrogen material represented by Formula 1:

wherein, each of Y 1 , Y 2 , and Y 3 is B;

each of X 1 , X 2 , and X 3 is N;

each of X 4 , X 5 and X 6 is independently selected from single bond, O, S or CR a ;

wherein R a is independently selected from one of the following groups: substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 monocyclic or polycyclic aromatic hydrocarbon, and C5-C30 monocyclic or polycyclic hetero-aromatic hydrocarbon;

each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 is independently selected from N or CR b , wherein at least one of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 is N, wherein R b is independently selected from one of hydrogen, deuterium, halogen, cyano, or one of the following groups: substituted or unsubstituted C1-C36 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C6 alkoxy or thioalkoxy, substituted or unsubstituted C6-C48 monocyclic or polycyclic aromatic hydrocarbon, substituted or unsubstituted C3-C48 monocyclic or polycyclic heteroaromatic hydrocarbon, and two adjacent R b groups are independent to each other or at least two adjacent R b groups are bonded to each other to form C3-C10 cycloalkane, C6-C30 aromatic hydrocarbon or C5-C30 hetero-aromatic hydrocarbon;

Z 19 is C; and

if substituents exist in the above group, each of the substituents is independently selected from one of deuterium, cyano, halogen, C1-C10 alkyl or cycloalkyl, C2-C6 alkenyl or cycloalkenyl, C1-C6 alkoxy or thioalkoxy, nitro, amine, carbonyl, carboxy, ester, C6-C30 aryl, and C3-C30 heteroaryl;

wherein a triplet energy level of the dye is higher than that of the triplet-triplet annihilation material;

wherein the dye has a mass proportion of 5%-20%, based on a total mass of the light-emitting layer.

2 . The organic light emitting device according to claim 1 , wherein the boron-nitrogen material has a structure represented by Formula 1-1,

wherein, each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 is independently selected from N or CR b .

3 . The organic light emitting device according to claim 2 , wherein in the Formula 1-1, Y 1 , Y 2 and Y 3 are all selected as a B atom, and X 1 , X 2 and X 3 are all selected as a N atom.

4 . The organic light emitting device according to claim 1 , wherein not more than six of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 are an N atom.

5 . The organic light emitting device according to claim 1 , wherein not more than three of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 are an N atom.

6 . The organic light emitting device according to claim 2 , wherein in Formula 1-1, at least one of Z 2 , Z 5 , Z 8 , Z 11 , Z 14 , Z 17 is an N atom.

7 . The organic light emitting device according to claim 6 , wherein an N atom in an N heterocyclic ligand is disposed at γ position in a carbazole group.

8 . The organic light emitting device according to claim 1 , wherein the R b is independently selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, methoxy, phenyl, naphthyl, anthryl, benzoanthryl, phenanthryl, benzophenanthryl, pyrenyl, cavity group, peryl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, bisphenyl, terphenyl, triphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimetric indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroisotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, methyl-substituted thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, methyl-substituted pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphtho-oxazolyl, anthraoxazolyl, phenanthro-oxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, (poly)halobenzene, (poly)cyanobenzene, (poly)trifluoromethylbenzene, or a combination of the above two substituent groups.

9 . The organic light emitting device according to claim 1 , wherein the boron-nitrogen material is selected from compounds represented by the following structures:

10 . The organic light emitting device according to claim 1 , wherein the singlet energy level of the triplet-triplet annihilation material is greater than that of the boron-nitrogen material, and the triplet energy level of the triplet-triplet annihilation material is less than that of the boron-nitrogen material.

11 . The organic light emitting device according to claim 1 , further comprising a hole transport region, the hole transport region is a multilayer structure comprising at least two layers of hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), wherein the material of the hole transport region is selected from a phthalocyanine derivative, a conductive polymer, a polymer containing a conductive dopant, and an aromatic amine derivative.

12 . The organic light emitting device according to claim 11 , wherein the material of the hole transport region is an aromatic amine derivative, which is one or more of HT-1 to HT-34 compounds,

13 . The organic light emitting device according to claim 11 , wherein the phthalocyanine derivative comprises CuPc, and the conductive polymer or the polymer containing a conductive dopant comprises polyphenylene vinylene, polyaniline with dodecylbenzene sulfonic acid (Pani with DBSA), poly(3,4-ethylenedioxythiophene) with poly(4-styrene sulfonate) (PEDOT with PSS), polyaniline with camphorsulfonic acid (Pani with CSA), polyaniline with Poly(4-styrene sulfonate) (Pani with PSS).

14 . The organic light emitting device according to claim 12 , wherein the device contains a hole transport layer, wherein the hole injection layer is located between an anode and the hole transport layer, and the hole injection layer is a single compound material or the combination of multiple compounds.

15 . The organic light emitting device according to claim 14 , wherein the device contains a hole transport layer, wherein the hole injection layer uses one or more of the HT-1 to HT-34 compounds, or uses one of HI-1 to HI-3, or use one or more of the HT-1 to HT-34 compounds doped with one or more of the following HI-1 to HI-3 compounds,

16 . The organic light emitting device according to claim 1 , further comprising an electron transport region, the electron transport region is a single-layered electron transport layer (ETL) which comprises a single-layer electron transport layer containing one compound and a single-layer electron transport layer containing multiple compounds, or the electron transport region is a multilayer structure comprising at least two layers of electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

17 . The organic light emitting device according to claim 16 , wherein the device contains an electron transport layer, wherein the material of electron transport layer is selected from one or more of ET-1 to ET-57,

18 . The organic light emitting device according to claim 1 , wherein the host material is a H2 having the following structure,

and the boron-nitrogen material is selected from compounds represented by the following structures:

19 . An organic light emitting device, comprising a light-emitting layer, wherein the light-emitting layer comprises a host material and a dye, the host material is a triplet-triplet annihilation material, and the dye is a boron-nitrogen material represented by Formula 1-1:

wherein, each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 is independently selected from N or CR b ;

wherein R b is independently selected from one of hydrogen, deuterium, halogen, cyano, or one of the following groups: substituted or unsubstituted C1-C36 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C6 alkoxy or thioalkoxy, substituted or unsubstituted C6-C48 monocyclic or polycyclic aromatic hydrocarbon, substituted or unsubstituted C3-C48 monocyclic or polycyclic heteroaromatic hydrocarbon, and two adjacent R b groups are independent to each other or at least two adjacent R b groups are bonded to each other to form C3-C10 cycloalkane, C6-C30 aromatic hydrocarbon or C5-C30 hetero-aromatic hydrocarbon;

wherein at least one of Z 2 , Z 5 , Z 8 , Z 11 , Z 14 , Z 17 is an N atom;

if substituents exist in the above group, each of the substituents is independently selected from one of deuterium, cyano, halogen, C1-C10 alkyl or cycloalkyl, C2-C6 alkenyl or cycloalkenyl, C1-C6 alkoxy or thioalkoxy, nitro, amine, carbonyl, carboxy, ester, C6-C30 aryl, and C3-C30 heteroaryl;

wherein a triplet energy level of the dye is higher than that of the triplet-triplet annihilation material.

20 . An organic light emitting device, comprising a light-emitting layer, wherein the light-emitting layer comprises a host material and a dye, the host material is a triplet-triplet annihilation material, and the dye is a boron-nitrogen material represented by Formula 1:

wherein, each of Y 1 , Y 2 , and Y 3 is B;

each of X 1 , X 2 , and X 3 is N;

each of X 4 , X 5 and X 6 is independently selected from single bond, O, S or CR a ;

wherein R a is independently selected from one of the following groups: substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 monocyclic or polycyclic aromatic hydrocarbon, and C5-C30 monocyclic or polycyclic hetero-aromatic hydrocarbon;

each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 , Z 14 , Z 15 , Z 16 , Z 17 , and Z 18 is independently selected from N or CR b , wherein R b is independently selected from one of hydrogen, deuterium, halogen, cyano, or one of the following groups: substituted or unsubstituted C1-C36 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C1-C6 alkoxy or thioalkoxy, substituted or unsubstituted C6-C48 monocyclic or polycyclic aromatic hydrocarbon, substituted or unsubstituted C3-C48 monocyclic or polycyclic heteroaromatic hydrocarbon, and two adjacent R b groups are independent to each other or at least two adjacent R b groups are bonded to each other to form C3-C10 cycloalkane, C6-C30 aromatic hydrocarbon or C5-C30 hetero-aromatic hydrocarbon;

Z 19 is C; and

if substituents exist in the above group, each of the substituents is independently selected from one of deuterium, cyano, halogen, C1-C10 alkyl or cycloalkyl, C2-C6 alkenyl or cycloalkenyl, C1-C6 alkoxy or thioalkoxy, nitro, amine, carbonyl, carboxy, ester, C6-C30 aryl, and C3-C30 heteroaryl;

wherein a triplet energy level of the dye is higher than that of the triplet-triplet annihilation material;

wherein the dye has a mass proportion of 5%-20%, based on a total mass of the light-emitting layer;

wherein the boron-nitrogen material is selected from compounds represented by the following structures:

Assignments (1)

Priority Claims (1)

Continuity (2)

References Cited (16)