Solution: As we know, the integral representation of the trigamma function is
$$
\psi^{(1)}(k) = \int_0^1 \frac{x^{k-1} \ln(x)}{1-x} \, dx
$$
Using this, we get:
$$
\left( \psi^{(1)}(k) \right)^2 = \int_0^1 \int_0^1 \frac{\ln(y) \ln(x)}{(1-x)(1-y)} (xy)^{k-1} \, dx \, dy
$$
Now, summing over $k$, we have:
\begin{align}
\sum_{k=1}^{\infty} (-1)^{k-1} \left( \psi^{(1)}(k) \right)^2
& = \int_0^1 \int_0^1 \frac{\ln(y) \ln(x)}{(1-x)(1-y)} \, dx \, dy \sum_{k=1}^{\infty} (-xy)^{k-1} \\
& = \int_0^1 \int_0^1 \frac{\ln(y) \ln(x)}{(1-x)(1-y)(1+xy)} \, dx \, dy \\
& = \int_0^1 \frac{\ln(x)}{1-x} \left( \int_0^1 \frac{\ln(y)}{(1-y)(1+xy)} \, dy \right) dx
\end{align}
Let
$$
A = \int_0^1 \frac{\ln(y)}{(1-y)(1+xy)} \, dy = \frac{x}{x+1} \int_0^1 \frac{\ln(y)}{1+xy} \, dy + \frac{1}{1+x} \int_0^1 \frac{\ln(y)}{1-y} \, dy
$$
We now compute the individual sums:
\begin{align}
A &= \frac{x}{x+1} \sum_{n=1}^{\infty} (-x)^{n-1} \int_0^1 y^{n-1} \ln(y) \, dy + \frac{1}{x+1} \sum_{n=1}^{\infty} \int_0^1 y^{n-1} \ln(y) \, dy \\
&= \frac{x}{x+1} \sum_{n=1}^{\infty} (-x)^{n-1} \left( \frac{-1}{n^2} \right) + \frac{1}{x+1} \sum_{n=1}^{\infty} \left( \frac{-1}{n^2} \right) \\
&= \frac{1}{x+1} \sum_{n=1}^{\infty} \frac{(-x)^n}{n^2} - \frac{\zeta(2)}{x+1} = \frac{Li_2(-x)}{x+1} - \frac{\zeta(2)}{x+1}
\end{align}
Using this result in the previous expression, we get:
\begin{align}
S &= \int_0^1 \frac{\ln(x)}{1-x} \left( \frac{1}{1+x} \left( Li_2(-x) - \zeta(2) \right) \right) dx \\
&= \int_0^1 \frac{\ln(x) Li_2(-x)}{1-x^2} \, dx - \zeta(2) \int_0^1 \frac{\ln(x)}{1-x^2} \, dx
\end{align}
Now, let us compute:
$$
B = \int_0^1 \frac{\ln(x)}{1-x^2} \, dx = \frac{1}{2} \int_0^1 \frac{\ln(x)}{1-x} \, dx + \frac{1}{2} \int_0^1 \frac{\ln(x)}{1+x} \, dx
$$
We can simplify the sums:
\begin{align}
B &= \frac{1}{2} \sum_{n=1}^{\infty} \int_0^1 x^{n-1} \ln(x) \, dx + \frac{1}{2} \sum_{n=1}^{\infty} (-1)^{n-1} \int_0^1 x^{n-1} \ln(x) \, dx \\
&= \frac{1}{2} \sum_{n=1}^{\infty} \left( \frac{-1}{n^2} \right) + \frac{1}{2} \sum_{n=1}^{\infty} (-1)^{n-1} \left( \frac{-1}{n^2} \right)
\end{align}
\begin{aligned}
& = \frac{-\zeta(2)}{2} + \frac{-\zeta(2)}{4} = \frac{-3 \zeta(2)}{4} = -\frac{\pi^2}{8} \ldots \ldots \ldots \ldots . . \, (5) \\
& \text{Let } C = \int_0^1 \frac{\ln(x) \, Li_2(-x)}{1 - x^2} \, dx \\
& = \frac{1}{2} \int_0^1 \frac{\ln(x) \, Li_2(-x)}{1+x} \, dx + \frac{1}{2} \int_0^1 \frac{\ln(x) \, Li_2(-x)}{1-x} \, dx \\
& = \frac{1}{2} \sum_{n=1}^{\infty} (-1)^n H_n^{(2)} \int_0^1 x^n \ln(x) \, dx + \frac{1}{2} \sum_{n=1}^{\infty} \frac{(-1)^n}{n^2} \int_0^1 \frac{x^n \ln(x)}{1-x} \, dx \\
& = \frac{1}{2} \sum_{n=1}^{\infty} (-1)^n \left( \frac{1}{n^2} - H_n^{(2)} \right) \int_0^1 x^{n-1} \ln(x) \, dx + \frac{1}{2} \sum_{n=1}^{\infty} \frac{(-1)^n}{n^2} \left( H_n^{(2)} - \zeta(2) \right) \\
& = \frac{1}{2} \sum_{n=1}^{\infty} (-1)^n \left( \frac{1}{n^2} - H_n^{(2)} \right) \left( \frac{-1}{n^2} \right) + \frac{1}{2} \sum_{n=1}^{\infty} \frac{(-1)^n}{n^2} \left( H_n^{(2)} - \zeta(2) \right) \\
& = \frac{1}{2} \sum_{n=1}^{\infty} \frac{(-1)^n H_n^{(2)}}{n^2} - \frac{1}{2} Li_4(-1) + \frac{1}{2} \sum_{n=1}^{\infty} \frac{(-1)^n H_n^{(2)}}{n^2} - \frac{1}{2} \zeta(2) Li_2(-1) \\
& = \sum_{n=1}^{\infty} \frac{(-1)^n H_n^{(2)}}{n^2} + \frac{17 \pi^4}{1440}
\end{aligned}
$$
We have:
$$
\sum_{n=1}^{\infty} \frac{(-1)^n H_n^{(2)}}{n^2} = \frac{51 \pi^4}{1440} - \frac{7}{2} \ln(2) \zeta(3) + \frac{\pi^2}{6} \ln^2(2) - \frac{1}{6} \ln^4(2) - 4 Li_4\left( \frac{1}{2} \right)
$$
Then,
$$
C = \frac{17 \pi^4}{360} - \frac{7}{2} \ln(2) \zeta(3) + \frac{\pi^2}{6} \ln^2(2) - \frac{1}{6} \ln^4(2) - 4 Li_4\left( \frac{1}{2} \right)
$$
Plugging (5) and (6) into (4), we get:
$$
S = \frac{49 \pi^4}{720} - \frac{7}{2} \ln(2) \zeta(3) + \frac{\pi^2}{6} \ln^2(2) - \frac{1}{6} \ln^4(2) - 4 Li_4\left( \frac{1}{2} \right)
$$