Organic electroluminescent compound and organic photoelectric apparatus

1. A nitrogen-containing heterocyclic compound having a general formula (I):

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a hydrogen atom, a compound having a general formula (II), and a compound having a general formula (III),

A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include two compounds having the general formula (II) and two compounds having the general formula (III),

the two compounds having the general formula (II) are included in one of A 1 , A 2 , A 3 , A 4 and A 5 , and one of A 6 , A 7 , A 8 , A 9 , and A 10 , respectively,

the two compounds having the general formula (III) are included in one of A 1 , A 2 , A 3 , A 4 and A 5 , and one of A 6 , A 7 , A 8 , A 9 , and A 10 , respectively, and the compound having the general formula (III) included in one of A 1 , A 2 , A 3 , A 4 and A 5 is different from the compound having the general formula (III) included in one of A 6 , A 7 , A 8 , A 9 and A 10 ,

the general formula (II) being:

wherein Y 1 , Y 2 , and Y 3 are independently selected from C and N; and R 3 and R 4 are independently selected from C 6-30 aromatic group and C 2-30 heterocyclic aromatic group, and

the general formula (III) being:

wherein X is selected from one of —O—, —S—, —C(CH 3 ) 2 , —Si(CH 3 ) 2 , and

and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are independently selected from hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group,

wherein A 3 and A 8 are one of the followings:

both A 3 and A 8 are hydrogen atoms;

when A 3 and A 8 include the two compounds having the general formula (II), the two compounds having the general formula (II) included in A 3 and A 8 are the same; and

when A 3 and A 8 include two compounds having the general formula (III), the two compounds having the general formula (III) included in A 3 and A 8 are different; and

wherein the nitrogen-containing heterocyclic compound is synthesized using a biphenyl derivative as a starting material, wherein the biphenyl derivative includes two nitro groups and two bromo groups.

2. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:

an energy level difference (ΔE st ) among 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:

4. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:

R 3 and R 4 are independently selected from one or more of substituted or non-substituted phenyl group, substituted or non-substituted pyridyl group, substituted or non-substituted pyrimidyl group, and substituted or non-substituted triazinyl group.

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 , wherein:

R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are all hydrogen.

7. 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 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a hydrogen atom, a compound having a general formula (II), and a compound having a general formula (III),

A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include two compounds having the general formula (II) and two compounds having the general formula (III),

the two compounds having the general formula (II) are included in one of A 1 , A 2 , A 3 , A 4 and A 5 , and one of A 6 , A 7 , A 8 , A 9 , and A 10 , respectively,

the two compounds having the general formula (III) are included in one of A 1 , A 2 , A 3 , A 4 and A 5 , and one of A 6 , A 7 , A 8 , A 9 , and A 10 , respectively, and the compound having the general formula (III) included in one of A 1 , A 2 , A 3 , A 4 and A 5 is different from the compound having the general formula (III) included in one of A 6 , A 7 , A 8 , A 9 and A 10 ,

the general formula (II) being:

wherein Y 1 , Y 2 , and Y 3 are independently selected from C and N; and R 3 and R 4 are independently selected from C 6-30 aromatic group and C 2-30 heterocyclic aromatic group, and

the general formula (III) being:

wherein X is selected from one of —O—, —S—, —C(CH 3 ) 2 , —Si(CH 3 ) 2 , and

and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are independently selected from hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group,

wherein A 3 and A 8 are one of the followings:

both A 3 and A 8 are hydrogen atoms;

when A 3 and A 8 include the two compounds having the general formula (II), the two compounds having the general formula (II) included in A 3 and A 8 are the same; and

when A 3 and A 8 include two compounds having the general formula (III), the two compounds having the general formula (III) included in A 3 and A 8 are different; and

wherein the at least one nitrogen-containing heterocyclic compound is synthesized using a biphenyl derivative as a starting material, wherein the biphenyl derivative includes two nitro groups and two bromo groups.

8. The organic photoelectric apparatus according to claim 7 , wherein the organic layer comprises:

at least one light-emitting layer; and

the at least one light-emitting layer includes the at least one nitrogen-containing heterocyclic compound, the at least one nitrogen-containing heterocyclic compound having the general formula (I).

9. The organic photoelectric apparatus according to claim 8 , wherein:

the at least one nitrogen-containing heterocyclic compound is used as one of a host material, a doping material, and a co-doping material of the at least one light-emitting layer.

10. The organic photoelectric apparatus according to claim 7 , 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.

11. The organic photoelectric apparatus according to claim 10 , wherein:

the nitrogen-containing heterocyclic compound is a host material of the at least one light-emitting layer.

12. The organic photoelectric apparatus according to claim 7 , wherein:

an energy level difference (ΔEst) 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.

13. The nitrogen-containing heterocyclic compound according to claim 1 , comprising one of:

14. A nitrogen-containing heterocyclic compound having a general formula (I):

wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 are independently selected from a hydrogen atom, a compound having a general formula (II), and a compound having a general formula (III), and

A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , and A 10 include two compounds having the general formula (II) and two compounds having the general formula (III),

the two compounds having the general formula (II) are included in two of A 1 , A 2 , A 3 , A 4 and A 5 , or in two of A 6 , A 7 , A 8 , A 9 , and A 10 ,

the two compounds having the general formula (III) are included in two of A 1 , A 2 , A 3 , A 4 and A 5 , or in two of A 6 , A 7 , A 8 , A 9 , and A 10 ,

A 1 , A 2 , A 3 , A 4 and A 5 have two compounds having the general formula (II) or the general formula (III), and A 6 , A 7 , A 8 , A 9 and A 10 have two compounds having the general formula (II) or the general formula (III),

the general formula (II) being:

wherein Y 1 , Y 2 , and Y 3 are independently selected from C and N; and R 3 and R 4 are independently selected from C 6-30 aromatic group and C 2-30 heterocyclic aromatic group, and

the general formula (III) being:

wherein X is selected from one of —NH—, —N(CH 3 )—,

—SiH 2 —, —Si(CH 3 ) 2 —, —SiH(CH 3 )—,

and R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are independently selected from hydrogen, deuterium, C 1-30 alkyl group, C 6-30 aromatic group, and C 2-30 heterocyclic aromatic group, and

the nitrogen-containing heterocyclic compound is synthesized using a biphenyl derivative as a starting material, wherein the biphenyl derivative includes at least one compound selected

15. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:

when A 3 and A 8 include the two compounds having the general formula (II) that are the same, A 1 , A 2 , A 4 , A 5 , A 6 , A 7 , A 9 , and A 10 include two compounds having the general formula (III).

16. The nitrogen-containing heterocyclic compound according to claim 1 , wherein:

the biphenyl derivative as the starting material includes at least one compound selected

17. The at least one nitrogen-containing heterocyclic compound according to claim 7 , wherein:

the biphenyl derivative as the starting material includes at least one compound selected