Organic electroluminescent compound and organic photoelectric apparatus thereof
A nitrogen-containing heterocyclic compound having a general formula (I) and an organic photoelectric apparatus are provided. The compound of general formula (I) is: wherein A 1 to A 4 are independently selected from a hydrogen atom, a function group having a general formula (II); A 1 to A 4 include at least one function group having the general formula (II); R 1 and R 2 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group; Y 1 and Y 2 are independently selected from substituted or non-substituted C and N, the general formula (II) being: wherein X is selected from one of oxyl group (—O—), sulfhydryl group (—S—), substituted or non-substituted imino group, substituted or non-substituted methylene group, and substituted or non-substituted silicylene group; and R 3 to R 10 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group.
1. A nitrogen-containing heterocyclic compound having a general formula (I):
wherein A 1 , A 2 , A 3 , and A 4 are independently selected from a hydrogen atom, and a functional group having a general formula (II); A 1 , A 2 , A 3 , and A 4 include at least one functional group having the general formula (II); R 1 and R 2 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group; Y 1 and Y 2 are independently selected from substituted or non-substituted C and N,
the general formula (II) being:
wherein X is selected from one of oxyl group (—O—), sulfhydryl group (—S—), substituted or non-substituted imino group, substituted or non-substituted methylene group, and substituted or non-substituted silicylene group; and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from any one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group.
2. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
an energy level difference (ΔE st ) between a lowest singlet state S 1 and a lowest triplet state T 1 is smaller than or equal to approximately 0.30 eV.
3. The nitrogen-containing heterocyclic compound according to claim 1 , wherein the compound having the general formula (II) comprises one of:
—O—, —S—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—,
—SiH 2 —, —Si(CH 3 ) 2 —, —SiH(CH 3 )—,
4. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are all hydrogen.
5. The nitrogen-containing heterocyclic compound according to claim 1 , wherein the compound having the general formula (II) is one of:
6. The nitrogen-containing heterocyclic compound according to claim 1 , comprising one of:
7. The nitrogen-containing heterocyclic compound according to claim 1 , comprising:
a thermally activated delayed fluorescence performance.
8. An organic photoelectric apparatus, comprising:
an anode substrate;
at least one organic layer formed over the anode substrate; and
a cathode layer formed over the organic layer,
wherein the at least one organic layer includes at least one nitrogen-containing heterocyclic compound having a general formula (I):
wherein A 1 , A 2 , A 3 , and A 4 are independently selected from a hydrogen atom, a functional group having a general formula (II); A 1 , A 2 , A 3 , and A 4 include at least one functional group having the general formula (II); R 1 and R 2 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group; Y 1 and Y 2 are independently selected from substituted or non-substituted C and N,
the general formula (II) being:
wherein X is selected from one of oxyl group (—O—), sulfhydryl group (—S—), substituted or non-substituted imino group, substituted or non-substituted methylene group, and substituted or non-substituted silicylene group; and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from any one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group.
9. The organic photoelectric apparatus according to claim 8 , wherein the organic layer comprises:
at least one light-emitting layer; and
the at least one light-emitting layer includes one or at least two nitrogen-containing heterocyclic compounds.
10. The organic photoelectric apparatus according to claim 9 , wherein:
the one or at least two nitrogen-containing heterocyclic compounds are used as one of a host material, a doping material, and a co-doping material of the at least one light-emitting layer.
11. The organic photoelectric apparatus according to claim 9 , wherein the organic layer further comprises:
one or at least two of a hole transport layer, a hole injection layer, a hole barrier layer, an electron transport layer, an electron injection layer and an electron barrier layer.
12. The organic photoelectric apparatus according to claim 11 , wherein:
the nitrogen-containing heterocyclic compound is a host material of the at least one light-emitting layer.
13. The organic photoelectric apparatus according to claim 8 , wherein:
an energy level difference (ΔE st ) among a lowest singlet state S 1 and a lowest triplet state T 1 of the nitrogen-containing heterocyclic compound is smaller than or equal to approximately 0.30 eV.
14. The organic photoelectric apparatus according to claim 8 , wherein:
the nitrogen-containing heterocyclic compound has a thermally activated delayed fluorescence performance.
15. A method for fabricating an organic photoelectric apparatus, comprising:
providing an anode substrate,
forming at least one organic layer over the anode substrate; and
forming a cathode layer over the organic layer,
wherein the at least one organic layer includes at least one nitrogen-containing heterocyclic compound having a general formula (I):
wherein A 1 , A 2 , A 3 , and A 4 are independently selected from a hydrogen atom, a functional group having a general formula (II); A 1 , A 2 , A 3 , and A 4 include at least one functional group having the general formula (II); R 1 and R 2 are independently selected from one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group and C 2-30 heterocyclic aromatic group; Y 1 and Y 2 are independently selected from substituted or non-substituted C and N
the general formula (II) being:
wherein X is selected from one of oxyl group (—O—), sulfhydryl group (—S—), substituted or non-substituted imino group, substituted or non-substituted methylene group, and substituted or non-substituted silicylene group; and R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from any one of hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group.
16. The method according to claim 15 , wherein:
the organic layer comprises at least one light-emitting layer; and
the at least one light-emitting layer includes one or at least two nitrogen-containing heterocyclic compounds.
17. The method according to claim 15 , wherein:
the one or at least two nitrogen-containing heterocyclic compounds are used as one of a host material, a doping material, and a co-doping material of the at least one light-emitting layer.
18. The method according to claim 15 , wherein forming the at least one organic layer further comprises:
forming a hole transport layer on the anode substrate;
forming a light-emitting layer on the hole transport layer;
forming a hole barrier layer on the light-emitting layer;
forming an electron transport layer on the hole barrier layer; and
forming an electron injection layer on the electron transport layer.
19. The method according to claim 15 , wherein:
the organic layer is formed by an evaporation process.
20. The method according to claim 15 , wherein:
the nitrogen-containing heterocyclic compound has a thermally activated delayed fluorescence performance.