Hole-transporting ink composition, light-emitting device, and method of preparing the light-emitting device
According to one aspect of the invention, a hole-transporting ink composition for a light emitting device, the hole-transporting ink composition includes an adhesion-promoting compound represented by Formula 1 and a hole-transporting compound: A 1 —B 1 —C 1 Formula 1 wherein, in Formula 1, the variables are defined above.
1. A hole-transporting ink composition for a light emitting device, the hole-transporting ink composition comprising:
an adhesion-promoting compound represented by Formula 1; and
a hole-transporting compound comprising a polymeric compound including a repeating unit made from a compound represented by Formula 201 or 202:
A 1 —B 1 —C 1 Formula 1
wherein, in Formula 1,
A 1 is —Si(Q 1 )(Q 2 )(Q 3 ), —S(Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —C(═O)(Q 1 ),
B 1 is a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, or a substituted or unsubstituted C 2 -C 60 alkynylene group,
C 1 is —O(Q 4 ), —S(Q 4 ), —C(═O)(Q 4 ), —N(Q 4 )(Q 5 ), a substituted or unsubstituted acryl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, or a substituted or unsubstituted C 1 -C 60 fluoroalkyl group, and
Q 1 to Q 5 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a is hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 —C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
in Formulae 201 and 202
L 201 to L 204 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
L 205 is a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
xa1 to xa4 are each independently 0, 1, 2, or 3, and
xa5 is an integer from 2 to 10,
in Formula 201,
R 201 and R 202 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
R 203 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
in Formula 202,
R 201 to R 204 and Q 201 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
provided that in Formula 202, each of R201 to R203 does not comprise a substituted or unsubstituted fluorenyl group.
2. The hole-transporting ink composition of claim 1 , wherein the adhesion-promoting compound comprises a silane compound or a thiol compound.
3. The hole-transporting ink composition claim 1 , wherein the adhesion-promoting compound comprises a self-assembled monomolecule for forming a self-assembled monolayer.
4. A hole-transporting ink composition for a light emitting device, the hole-transporting ink composition comprising:
an adhesion-promoting compound represented by Formula 1; and
a hole-transporting compound comprising a polymeric compound having a weight average molecular weight of about 20,000 and a repeating unit represented by Formula HIL1:
A 1 —B 1 —C 1 Formula 1
wherein, in Formula 1,
A 1 is —Si(Q 1 )(Q 2 )(Q 3 ), —S(Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —C(═O)(Q 1 ),
B 1 is a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, or a substituted or unsubstituted C 2 -C 60 alkynylene group,
C 1 is —O(Q 4 ), —S(Q 4 ), —C(═O)(Q 4 ), —N(Q 4 )(Q 5 ), a substituted or unsubstituted acryl group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, or a substituted or unsubstituted C 1 -C 60 fluoroalkyl group, and
Q 1 to Q 5 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a is hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group,
in Formulae HIL1,
n is an integer greater than zero and
R and R′ are each independently —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
5. The hole-transporting ink composition of claim 1 , wherein the hole-transporting ink composition further comprises a solvent,
the solvent comprises a non-polar solvent, and
the adhesion-promoting compound is soluble in the non-polar solvent.
6. The hole-transporting ink composition of claim 5 , wherein based on 100 parts by weight of the hole-transporting ink composition, an amount of the adhesion-promoting compound is in a range of about 0.1 parts by weight to about 10 parts by weight, and
an amount of the hole-transporting compound is in a range of about 0.1 parts by weight to about 50 parts by weight.
7. The hole-transporting ink composition of claim 1 , wherein the hole-transporting ink composition does not include a luminescent material.
8. The hole-transporting ink composition of claim 5 , wherein the hole-transporting ink composition consists of the adhesion-promoting compound, the hole-transporting compound, and the solvent.