Thermally Activated Delayed Material and Organic Photoelectric Device Comprising the Same

1 . A thermally activated delayed material being a compound having the structure of formula (I):

in formula (I), X is a boron atom or a nitrogen atom;

in formula (I), D 1 and D 2 are each independently any one selected from the following groups:

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl;

m 1 and m 2 are each independently an integer of 0-4; and in the same group, the sum of m 1 and m 2 is less than or equal to 4;

in formula (I), R 1 and R 2 are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl;

in formula (I), n 1 and n 2 are each independently an integer of 0-4, and the sum of n 1 and n 2 is less than or equal to 4;

in formula (I), n 3 and n 4 are each independently an integer greater than or equal to 0;

in formula (I), L 1 and L 2 are each independently any one selected from substituted or unsubstituted aromatic groups; and the number of the substituents on the aromatic group in L 1 and L 2 is represented by m 3 .

2 . The thermally activated delayed material of claim 1 , wherein the sum of n 1 , n 2 , m 1 , m 2 and m 3 is less than or equal to 4.

3 . The thermally activated delayed material of claim 1 , wherein the sum of n 1 , n 2 , m 1 and m 2 is 0 or 1.

4 . The thermally activated delayed material of claim 1 , wherein m 1 =0 or m 2 =0, or R 1 , R 2 , R 3 or R 4 are each independently any one selected from the group consisting of methyl, ethyl, phenyl and tolyl.

5 . The thermally activated delayed material of claim 1 , wherein R 5 , R 6 , R 7 , R 8 and R 9 are each independently any one selected from the group consisting of methyl, ethyl, phenyl and tolyl.

6 . The thermally activated delayed material of claim 1 , wherein in formula (I), L 1 group is located on para position or meta position.

7 . The thermally activated delayed material of claim 1 , wherein in formula (I), D 1 -L 1 - group is the same as D 2 -L 2 - group.

8 . The thermally activated delayed material of claim 1 , wherein in formula (I), both n 1 and n 2 are 0, and D 1 -L 1 - group and D 2 -L 2 - group are the same.

9 . The thermally activated delayed material of claim 1 , wherein L 1 and L 2 are each independently selected from any one of the following groups, or any one of the following groups substituted with a substituent:

10 . The thermally activated delayed material of claim 1 , wherein L 1 and L 2 are each independently selected from any one of the following groups, or any one of the following groups substituted with a substituent:

11 . The thermally activated delayed material of claim 1 , wherein the energy level difference between the lowest singlet state S 1 and the lowest triplet state T 1 of the thermally activated delayed material ΔE ST is less than or equal to 0.30 eV.

12 . The thermally activated delayed material of claim 1 , wherein the thermally activated delayed material comprises any one selected from the group consisting of the following compounds, and a combination of at least two thereof:

13 . The thermally activated delayed material of claim 1 , wherein the thermally activated delayed material comprises any one selected from the group consisting of the following compounds, and a combination of at least two thereof:

14 . The thermally activated delayed material of claim 1 , wherein the thermally activated delayed material comprises any one selected from the group consisting of the following compounds, and a combination of at least two thereof:

15 . An organic photoelectric device comprising an anode, a cathode, and at least one organic thin film layer between the anode and the cathode; the organic thin film layer comprises a light emitting layer, and any one selected from the group consisting of a hole transporting layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, an electron injection layer, and a combination of at least two thereof;

the light emitting layer comprises any one or a combination of at least two of the following thermally activated delayed materials being a compound having the structure of formula (I):

in formula (I), X is a boron atom or a nitrogen atom;

in formula (I), D 1 and D 2 are each independently any one selected from the following groups:

wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl;

m 1 and m 2 are each independently an integer of 0-4; and in the same group, the sum of m 1 and m 2 is less than or equal to 4;

in formula (I), R 1 and R 2 are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclic group, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl;

in formula (I), n 1 and n 2 are each independently an integer of 0-4, and the sum of n 1 and n 2 is less than or equal to 4;

in formula (I), n 3 and n 4 are each independently an integer greater than or equal to 0;

in formula (I), L 1 and L 2 are each independently any one selected from substituted or unsubstituted aromatic groups; and the number of the substituents on the aromatic group in L 1 and L 2 is represented by m 3 ;

and the compound is used as any one of a dopant material, a co-doping material, or a host material.

16 . The organic photoelectric device of claim 15 , wherein the cathode is covered with a capping layer which has a refractive index of 1.85-2.05.

17 . The organic photoelectric device of claim 15 , wherein the light emitting layer is made of the thermally activated delayed material according to claim 1 and a host material.

18 . The organic photoelectric device of claim 15 , wherein the light emitting layer comprises a host material and a guest material; the thermally activated delayed material is used as the guest material for the light emitting layer, and the difference between the HOMO of the host material and the HOMO of the guest material is less than 0.6 eV, or the difference between the LUMO of the host material and the LUMO of the guest material is less than 0.6 eV.

19 . The organic photoelectric device of claim 18 , wherein the thermally activated delayed material is used as a guest material for the light emitting layer, and the host material is any one selected from the group consisting of 2,8-bis(diphenylphosphinyl)dibenzothiophene, 4,4′-bis(9-carbazole)biphenyl, 3,3′-bis(N-carbazolyl)-1,1′-biphenyl, 2,8-bis(diphenylphosphinoxy)dibenzofuran, bis (4-(9H-carbazolyl-9-yl)phenyl)diphenylsilane, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9h-carbazole, bis(2-diphenylphosphine oxide)diphenylether, 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene, 4,6-bis(3,5-di (3-pyridin)ylphenyl)-2-methylpyrimidine, 9-(3-(9H-carbazolyl-9-yl)phenyl)-9H-carbazole-3-cyano, 9-phenyl-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, diphenyl [4-(triphenylsilyl)phenyl]phosphine oxide, 4,4′,4″-tris(carbazol-9-yl)triphenylamine, 2,6-dicarbazole-1,5-pyridine, polyvinylcarbazole, polyfluorene, and a combination of at least two thereof.

20 . The organic photoelectric device of claim 15 , wherein the light emitting layer comprises the thermally activated delayed material according to claim 1 , and the hole injection material, the hole transporting material, and the electron blocking material are each independently any one selected from the group consisting of N,N′-diphenyl-N,N′-(1-naphthyl)-1,1′-biphenyl-4,4′-diamine, 4,4′,4″-tris(carbazol-9-yl)triphenylamine, 1,3-dicarbazol-9-yl benzene, 4,4′-bis(9-carbazole)biphenyl, 3,3′-bis(N-carbazolyl)-1,1′-biphenyl, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene, 4,4′-cyclohexyldi[N,N-di(4-methylphenyl)aniline, N,N′-diphenyl-N,N′-(1-naphthyl)-1,1′-biphenyl-4,4′-diamine, N,N′-bis(naphthalen-2-yl)-N,N′-bis(phenyl)biphenyl-4,4′-diamine, poly(3,4-ethylenedioxythiophene)-polystyrene sulfonic acid, polyvinylcarbazole, 9-phenyl-3,9-bicarbazole, molybdenum trioxide, and a combination of at least two thereof; and the hole blocking material, the electron transporting material, and the electron injection material are each independently any one selected from the group consisting of 2,8-bis(diphenylphosphinyl)dibenzothiophene, TSPO1, TPBi, 2,8-bis(diphenylphosphinoxy)dibenzofuran, bis(2-diphenylphosphine oxide)diphenylether, lithium fluoride, 4,6-bis(3,5-bis(3-pyridin)ylphenyl)-2-methylpyrimidine, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene, tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane, 1,3-bis(3,5-dipyridin-3-ylphenyl)benzene, 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine, diphenyl bis[4-(pyridin-3-yl)phenyl]silane, cesium carbonate, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1′-biphenyl-4-hydroxy)aluminum, 8-hydroxyquinoline-lithium, tris(8-hydroxyquinoline)aluminum, and a combination of at least two thereof.