Heterocyclic compound and organic light-emitting device containing the same
View Patent ↗A heterocyclic compound represented by one of Formulae 1-4 below and an organic light-emitting device including an organic layer that includes the heterocyclic compound. The heterocyclic compounds have excellent light-emitting characteristics and excellent electron transporting characteristics, and thus may be used as electron injecting materials or electron transporting materials suitable for all-color fluorescent and phosphorescent devices, such as red, green, blue, and white fluorescent and phosphorescent devices. In particular, the heterocyclic compounds are efficiently used as light-emitting materials of green, blue, and while fluorescent devices. By using the heterocyclic compounds, organic light-emitting devices having high efficiency, low driving voltage, high brightness, and long lifespan may be prepared.
1. A compound represented by one of Formulae 1-4:
Wherein, in Formula 1, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, and
A and B are each independently a substituted or unsubstituted heteroaromatic condensed polycyclic group selected from the group consisting of a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted carbazole, and a substituted or unsubstituted indazole, or the A and the B are an unsubstituted 9,9-dimethyl-9H-fluorene;
Wherein, in Formulae 2-4, R 1 to R 6 , R 10 to R 15 , R 20 to R 25 and R 30 to R 35 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group;
X 1 and X 3 are each independently —O—, —N(R 40 )—, —C(R 41 R 42 )—, or —S—, X 2 and X 4 are —CR 41 ═; and R 40 to R 42 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group; and
Wherein, in Formula 2, optionally, R 14 and R 40 , R 41 , or R 42 ; or R 11 and R 40 , R 41 , or R 42 are connected to each other to form a ring;
in Formula 3, optionally, R 23 and R 40 , R 41 , or R 42 ; or R 20 and R 40 , R 41 , or R 42 are connected to each other to form a ring; and
in Formula 4, optionally, R 35 and R 40 , R 41 , or R 42 ; or R 32 and R 40 , R 41 , or R 42 are connected to each other to form a ring.
2. The compound of claim 1 , wherein, in Formulae 2, 3, and 4, R 1 to R 6 , R 10 to R 15 , R 20 to R 25 , and R 30 to R 35 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, and one of Formulae 2a to 2j below:
wherein in Formula 2e Q 1 is —N(-*)-; and in Formula 2f Q 1 is —C(R 50 )(R 51 )—, —N(R 52 )—, —S—, or —O—;
Y 1 , Y 2 , and Y 3 are each independently —N═, —N(-*)-, —S—, —O—, or —C(R 53 )═; and wherein Y 1 , Y 2 , and Y 3 are each independently —N═, or —C(R 53 )═ in Formula 2c; Y 1 is not —N═, or —C(R 53 )═ in Formulae 2a; Y 1 is —N═, or —C(R 53 )═ in Formula 2g; Y 1 is —N(-*)-, and Y 2 is —N═, or —C(R 53 )═ in Formulae 2h; Y 1 is —C(R 53 )═, and Y 2 is —N═, or —C(R 53 )═ in Formula 2j;
Z 1 , Z 2 , Ar 12 , Ar 13 , R 50 , R 51 , R 52 , and R 53 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a carboxy group;
Ar 11 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 6 -C 20 arylene group, and a substituted or unsubstituted C 3 -C 20 heteroarylene group;
p is an integer from 1 to 3 in Formula 2a, an integer from 1 to 10 in Formulae 2c, 2d, and 2e, an integer from 1 to 7 in Formula 2f, an integer from 1 to 6 in Formula 2g, an integer from 1 to 5 in Formulae 2b, 2h, 2i, and 2j, respectively;
r is an integer from 0 to 5; and
* is a binding site.
3. The compound of claim 1 , wherein the compound is represented by one of Formulae 2 through 4, and, in Formulae 2, 3, and 4, R 2 , R 3 , R 5 , R 6 , R 10 , R 12 , R 13 , R 15 , R 21 , R 22 , R 24 , R 25 , R 30 , R 31 , R 33 , and R 34 are each independently a hydrogen atom or a heavy hydrogen atom.
4. The compound of claim 1 , wherein the compound is represented by one of Formulae 2 through 4, and, the compounds represented by Formulae 2, 3, and 4 are symmetrical compounds.
5. The compound of claim 1 , wherein the compound is represented by one of Formulae 2 through 4, and, in Formulae 2, 3, and 4, R 2 , R 3 , R 5 , R 6 , R 10 , R 12 , R 13 , R 15 , R 21 , R 22 , R 24 , R 25 , R 30 , R 31 , R 33 , and R 34 are each independently a hydrogen atom or a heavy hydrogen atom; and
R 1 , R 4 , R 11 , R 14 , R 20 , R 23 , R 32 , and R 35 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, and one of Formulae 2a to 2j below:
wherein in Formula 2e Q 1 is —N(-*)-; and in Formula 2f Q 1 is —C(R 50 )(R 51 )—, —N(R 52 )—, —S—, or —O—;
Y 1 , Y 2 , and Y 3 are each independently —N═, —N(-*)-, —S—, —O—, or —C(R 53 )═; and wherein Y 1 , Y 2 , and Y 3 are each independently —N═, or —C(R 53 )═ in Formula 2c; Y 1 is not —N═, or —C(R 53 )═ in Formulae 2a; Y 1 is —N═, or —C(R 53 )═ in Formula 2g; Y 1 is —N(-*)-, and Y 2 is —N═, or —C(R 53 )═ in Formulae 2h; Y 1 is —C(R 53 )═, and Y 2 is —N═, or —C(R 53 )═ in Formula 2j;
Z 1 , Z 2 , Ar 12 , Ar 13 , R 50 , R 51 , R 52 , and R 53 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a carboxy group;
Ar 11 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 6 -C 20 arylene group, and a substituted or unsubstituted C 3 -C 20 heteroarylene group;
p is an integer from 1 to 3 in Formula 2a, an integer from 1 to 10 in Formulae 2c, 2d, and 2e, an integer from 1 to 7 in Formula 2f, an integer from 1 to 6 in Formula 2g, an integer from 1 to 5 in Formulae 2b, 2h, 2i, and 2j, respectively;
r is an integer from 0 to 5; and
* is a binding site.
6. The compound of claim 1 , wherein the compound is represented by one of Formulae 2 through 4, and, in Formulae 2, 3, and 4, R 2 , R 3 , R 5 , R 6 , R 10 , R 12 , R 13 , R 15 , R 21 , R 22 , R 24 , R 25 , R 30 , R 31 , R 33 , and R 34 are each independently a hydrogen atom or a heavy hydrogen atom;
R 1 , R 4 , R 11 , R 14 , R 20 , R 23 , R 32 , and R 35 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, and one of Formulae 2a to 2j below; and
the compounds represented by Formulae 2, 3, and 4 are symmetrical compounds:
wherein in Formula 2e Q 1 is —N(-*)-; and in Formula 2f Q 1 is —C(R 50 )(R 51 )—, —N(R 52 )—, —S—, or —O—;
Y 1 , Y 2 , and Y 3 are each independently —N═, —N(-*)-, —S—, —O—, or —C(R 53 )═; and wherein Y 1 , Y 2 , and Y 3 are each independently —N═, or —C(R 53 )═ in Formula 2c; Y 1 is not —N═, or —C(R 53 )═ in Formulae 2a; Y 1 is —N═, or —C(R 53 )═ in Formula 2g; Y 1 is —N(-*)-, and Y 2 is —N═, or —C(R 53 )═ in Formulae 2h; Y 1 is —C(R 53 )═, and Y 2 is —N═, or —C(R 53 )═ in Formula 2j;
Z 1 , Z 2 , Ar 12 , Ar 13 , R 50 , R 51 , R 52 , and R 53 are each independently selected from the group consisting of a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 3 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxy group, and a carboxy group;
Ar 11 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 6 -C 20 arylene group, and a substituted or unsubstituted C 3 -C 20 heteroarylene group;
p is an integer from 1 to 3 in Formula 2a, an integer from 1 to 10 in Formulae 2c, 2d, and 2e, an integer from 1 to 7 in Formula 2f, an integer from 1 to 6 in Formula 2g, an integer from 1 to 5 in Formulae 2b, 2h, 2i, and 2j, respectively;
r is an integer from 0 to 5; and
* is a binding site.
7. The compound of claim 1 , wherein the compound is represented by one of the compounds below:
8. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a first layer comprising the compound of claim 1 .
9. The organic light-emitting device of claim 8 , wherein the first layer comprises a hole injection layer, a hole transport layer, a functional layer having both hole injecting and hole transporting capabilities, an emission layer, an electron injection layer, an electron transport layer, or a functional layer having both electron injecting and electron transporting capabilities.
10. The organic light-emitting device of claim 8 , wherein the first layer is an emission layer, and the compound is used as a fluorescent host or a fluorescent dopant.
11. The organic light-emitting device of claim 8 , wherein the organic layer comprises an emission layer, a hole transport layer, and an electron transport layer; and
the first layer is an emission layer, wherein the emission layer further comprises an anthracene compound, an arylamine compound or a styryl compound.
12. The organic light-emitting device of claim 8 , wherein the organic layer comprises an emission layer, a hole transport layer, and an electron transport layer; and
the first layer is an emission layer comprising at least one of a red layer, a green layer, a blue layer and a white layer, and said at least one of the red, green, blue, and white layers of the emission layer further comprises a phosphorescent compound.
13. The organic light-emitting device of claim 8 , wherein the first layer is a blue emission layer.
14. The organic light-emitting device of claim 8 , wherein the first layer is a blue emission layer, and the compound is used as a blue dopant.
15. The organic light-emitting device of claim 8 , wherein the organic layer comprises a hole injection layer, a hole transport layer, a functional layer having both hole injecting and hole transporting capabilities, an emission layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination of at least two thereof.
16. The organic light-emitting device of claim 15 , wherein at least one of the hole injection layer, the hole transport layer, and the functional layer having both hole injecting and hole transporting capabilities further comprises a charge-generating material.
17. The organic light-emitting device of claim 15 , wherein the electron transport layer comprises an electron transporting material and a metal-containing material.
18. A compound represented by one of Formulae 2-4:
Wherein, in Formulae 2-4, R 1 to R 6 , and R 20 to R 25 are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group;
X 1 and X 3 are —N(R 40 )—, and X 2 and X 4 are —N═; and R 40 is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1 -C 50 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, an amino group substituted with a C 6 -C 50 aryl group, a substituted or unsubstituted C 3 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group.