Azide-based compound, organic light-emitting device including the azide-based compound, and method of manufacturing the organic light-emitting device

1. An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an organic layer disposed between the first electrode and the second electrode and comprising an emission layer; and

an azide-based compound represented by Formula 1:

wherein the organic layer further comprises a hole transport region between the first electrode and the emission layer,

wherein the hole transport region comprises the at least one of the azide-based compound and a polymer having a molecular weight of about 5,000 g/mol or greater:

wherein, in Formula 1,

each of L 1 , L 2 , and L 3 and L 11 to L 12 is independently a single bond or a substituted or unsubstituted C 1 -C 10 alkylene group,

each of a1, a2, and a3 and a11 to a12 is independently an integer from 1 to 5, wherein, when a1 is two or more, two or more L 1 (s) are identical to or different from each other, when a2 is two or more, two or more L 2 (s) are identical to or different from each other, when a3 is two or more, two or more L 3 (s) are identical to or different from each other, when a11 is two or more, two or more L 11 (s) are identical to or different from each other, and when a12 is two or more, two or more L 12 (s) are identical to or different from each other,

each of b1 and b2 is independently an integer of 1 or 2,

b3 is an integer of 0 or 1,

when b3 is 0, *-((L 3 ) a3 -N 3 ) b3 is hydrogen,

when b1 is two or more, two or more *-((L 1 ) a1 -N 3 )(s) are identical to or different from each other, and when b2 is two or more, two or more *-((L 2 ) a2 -N 3 )(s) are identical to or different from each other,

* indicates a binding site to a neighboring atom, and

at least one substituent of the substituted C 1 -C 10 alkylene group is selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group.

2. The organic light-emitting device of claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the organic layer comprises at least one of the azide-based compound represented by Formula 1,

the organic layer further comprises a hole transport region between the emission layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The organic light-emitting device of claim 1 , wherein

the emission layer comprises a host material and a dopant material, and

the dopant material comprises a phosphorescent dopant or a fluorescent dopant.

4. The organic light-emitting device of claim 1 , wherein each of L 1 , L 2 , and L 3 is independently a single bond.

5. The organic light-emitting device of claim 1 , wherein

each of L 11 and L 12 is independently selected from:

a single bond, a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group; and

a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, and a C 1 -C 10 alkyl group.

6. The organic light-emitting device of claim 1 , wherein

*-(L 11 ) a11 -*′ and *-(L 12 ) a12 -*′ are identical to each other.

7. The organic light-emitting device of claim 1 , wherein

the azide-based compound has a molecular weight of about 100 g/mol to about 2,000 g/mol.

8. The organic light-emitting device of claim 1 , wherein

a sum of b1, b2, and b3 is 2, 3, or 4.

9. The organic light-emitting device of claim 6 , wherein

the azide-based compound is represented by Formula 1-1:

wherein, in Formula 1-1,

each of b1 and b2 is independently an integer of 1 or 2,

b3 is an integer of 0 or 1,

when b3 is 0, *-((L 3 ) a3 -N 3 ) b3 is hydrogen,

when b1 is two or more, two or more *-((L 1 ) a1 -N 3 )(s) are identical to or different from each other, and when b2 is two or more, two or more *-((L 2 ) a2 -N 3 )(s) are identical to or different from each other,

* indicates a binding site to a neighboring atom,

each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group.

10. The organic light-emitting device of claim 1 , wherein

the azide-based compound is selected from Compounds 1, 2, and 3:

11. A composition comprising:

the azide-based compound of claim 1 ;

a polymeric compound represented by Formula 2; and

a solvent:

wherein, in Formula 2,

each of Ar 1 , Ar 2 , and Ar 3 is independently a substituted or unsubstituted C 3 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

to each of c1 and c2 is independently an integer from 1 to 3,

n is an integer from 70 to 400,

at least one substituent of the substituted C 3 -C 60 carbocyclic group and the substituted C 1 -C 60 heterocyclic group is selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

12. The composition of claim 11 , wherein

Ar 1 to Ar 3 are each independently selected from:

a benzene group, a naphthalene group, a fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

13. The composition of claim 11 , wherein

the polymeric compound represented by Formula 2 is selected from Compounds 101, 102, and 103:

14. The composition of claim 11 , wherein

the polymeric compound has a molecular weight of about 5,000 g/mol or greater, and

the azide-based compound has a molecular weight of 2,000 g/mol or less.

15. A method of manufacturing an organic light-emitting

device, the method comprising:

forming a hole transport region on a first electrode,

wherein the forming of the hole transport region comprises a solution process using a composition, and

the composition comprises:

the azide-based compound of claim 1 ;

a polymeric compound represented by Formula 2; and

a solvent:

wherein, in Formula 2,

each of Ar 1 , Ar 2 , and Ar 3 is independently a substituted or unsubstituted C 3 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

each of c1 and c2 is an integer from 1, 2, or 3,

n is an integer from 70 to 400,

at least one substituent of the substituted C 3 -C 60 carbocyclic group and the substituted C 1 -C 60 heterocyclic group is selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and

Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

16. The method of claim 15 , wherein

the forming of the hole transport region further comprises:

performing heat curing or photocuring on the azide-based compound and the polymeric compound; or

removing the solvent,

wherein the removing of the solvent is performed in a temperature range of about 160° C. to about 280° C.

17. The method of claim 15 , further comprising forming an emission layer on the hole transport region,

wherein the forming of the emission layer comprises a solution process using a second composition, and

the second composition comprises a host material, a dopant material, and a second solvent.