BACKGROUND

1. Field

Embodiments relate to a heterocyclic compound and an organic electroluminescence device including the same.

2. Description of the Related Art

The development of an organic electroluminescence display as an image display is being actively conducted. The organic electroluminescence display is different from a liquid crystal display and is a self-luminescent display accomplishing displays via the recombination of holes and electrons injected from a first electrode and a second electrode in an emission layer and via light emission from a luminescent material including an organic compound in the emission layer.

As an organic electroluminescence device, an organic device including, for example, a first electrode, a hole transport layer disposed on the first electrode, an emission layer disposed on the hole transport layer, an electron transport layer disposed on the emission layer, and a second electrode disposed on the electron transport layer is well known. Holes are injected from the first electrode, and the injected holes move via the hole transport layer and are injected into the emission layer. Meanwhile, electrons are injected from the second electrode, and the injected electrons move via the electron transport layer and are injected into the emission layer. The holes and electrons injected into the emission layer recombine to produce excitons in the emission layer. The organic electroluminescence device emits light using light generated by the transition of the excitons to a ground state. In addition, an embodiment of the configuration of the organic electroluminescence device is not limited thereto, but various modifications may be possible.

SUMMARY

Embodiments are directed to a heterocyclic compound and an organic electroluminescence device including the same.

The embodiments may be realized by providing a heterocyclic compound represented by the following Formula 1:



wherein in Formula 1, X is NR5, O, or S, R1to R4are each independently a hydrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1to R4being separate or forming a ring via combination of adjacent groups with each other, R5is a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, at least one of R1to R4is a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted sulfoxy group, or a substituted or unsubstituted phosphine oxide group, and at least two of R1to R4are not an aryl group or a heteroaryl group.

Two of R1to R4may each independently be an aryl group or a heteroaryl group, and at least one of the remaining ones of R1to R4may be a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted sulfoxy group, or a substituted or unsubstituted phosphine oxide group.

Two of R1to R4may each independently be a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms, and at least one of the remaining ones of R1to R4may be a substituted or unsubstituted silyl group.

Two of R1to R4may each independently be a substituted or unsubstituted phenyl group, and at least one of the remaining ones of R1to R4may be a triphenylsilyl group.

X may be NR5.

R5may be a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms.

R5may be a substituted or unsubstituted phenyl group.

X may be NR5, at least one of R1to R5may be a group represented by -L1-Y1, L1may be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and Y1may be a substituted or unsubstituted silyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted thienyl group, or a substituted or unsubstituted furanyl group.

The compound represented by Formula 1 may be represented by the following Formula 2:



wherein in Formula 2, n may be an integer of 1 to 3, when n is 2 or 3, a plurality of R1to R4may be the same or different from each other, L3may be a direct linkage or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and R1to R4may be defined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by the following Formula 3:



wherein in Formula 3, m may be an integer of 1 to 3, when m is 2 or 3, a plurality of R1, R2, and R4may be the same or different from each other, L4may be a direct linkage or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and X, R1, R2, and R4may be defined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by the following Formula 4:



wherein in Formula 4, q may be an integer of 1 to 3, when q is 2 or 3, a plurality of R1to R3may be the same or different from each other, L5may be a direct linkage or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and X, and R1to R3may be defined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by the following Formula 5:



wherein Formula 5, W may be O, S, PR8, S═O, SO2, P═OR9, CR10R11, or SiR12R13, R6to R13may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a and b may each independently be an integer of 0 to 4, and X, R1and R4may be defined the same as those of Formula 1.

The heterocyclic compound represented by Formula 1 may be a compound of the following Compound Group 1:



The embodiments may be realized by providing an organic electroluminescence device including a first electrode; a hole transport region on the first electrode; an emission layer on the hole transport region; an electron transport region on the emission layer; and a second electrode on the electron transport region, wherein the hole transport region includes a heterocyclic compound represented by the following Formula 1:



wherein in Formula 1, X is NR5, O or S, R1to R4are each independently a hydrogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1to R4being separate or forming a ring via combination of adjacent groups with each other, R5is a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted sulfoxy group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, at least one of R1to R4is a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted sulfoxy group, or a substituted or unsubstituted phosphine oxide group, and at least two of R1to R4are not an aryl group or a heteroaryl group.

Two of R1to R4may each independently be an aryl group or a heteroaryl group, and at least one of the remaining ones of R1to R4may be a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkythio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted boryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted sulfoxy group, or a substituted or unsubstituted phosphine oxide group.

X may be NR5, at least one of R1to R5may be a group represented by -L1-Y1, L1may be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, and Y1may be a substituted or unsubstituted silyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted thienyl group, or a substituted or unsubstituted furanyl group.

X may be NR5, and R5may be the same as defined in Formula 1.

The compound represented by Formula 1 may be represented by one of the following Formulae 2 to 4:



wherein in Formulae 2 to 4, n, m, and p may each independently be an integer of 1 to 3, when n is 2 or 3, a plurality of R1to R4may be the same or different from each other, when m is 2 or 3, a plurality of R1, R2, and R4may be the same or different from each other, when q is 2 or 3, a plurality of R1to R3may be the same or different from each other, L3to L5may each independently be a direct linkage or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and X, and R1to R4may be defined the same as those of Formula 1.

The compound represented by Formula 1 may be represented by the following Formula 5:



wherein in Formula 5, W may be O, S, PR8, S═O, SO2, P═OR9, CR10R11, or SiR12R13, R6to R13may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a and b may each independently be an integer of 0 to 4, and X, R1and R4may be defined the same as those of Formula 1.

The heterocyclic compound represented by Formula 1 may be a compound of the following Compound Group 1:



